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Category: Building teams

Do I care about my team more than my company?

Do I care about my team more than my company?

When a start-up company scales from a core team of 10-20 team members to 100+ people, I’ve witnessed a tendency for departments to lose touch with one another. Thats when we become hyper-focused on scaling our own individual team.

This often results in the loss of cross-team communication, break-downs in collaboration, along with other inter-department conflicts.

In this blog post, I’m going to share one exercise that will help our teams avoid conflicts and stay cohesive. It starts by seeing the organization as one entity, rather than a group of separate teams.

Do I see the company as one?

Adopting this perception is critical to the success of an organization, because the alternative, to see the company as parts that work separately, will never grow the company as a whole. Allow me to elaborate:

In our day-to-day, we often view ourselves as part of one specific team, one group. In turn, we subconsciously view the organization as a group of separate entities such as marketing, sales, customer success, product management, engineering, R&D, finance, etc.

The danger of this perception is that it can create inter-team conflicts: e.g. when goals are missed, we tend to blame it on other teams; when budgets are planned, we tend to fight each other for a bigger piece of the pie.

As we don’t emotionally relate to other teams as much as we do with our own team, we focus on improving only one team: Our team. This can be detrimental. Improving only one segment of the company will not result in a better company: e.g. Hitting our sales goals may not result in higher revenue if the sales team is not collaborating with customer success on retention goals.

A company thus needs all teams to be aligned on a single strategy for it to grow. It becomes clear that improving how teams interact and work with each other is more important than improving the team itself.

In one case, I was helping a clothing retailer’s merchandising team identify product trends. The goal was to find characteristics of clothing items that people would buy as part of repeat purchases, then advertise them as part of newsletters. However, because the marketing team had differing priorities, the products we identified as leading to a higher chance of repeat purchases failed to be advertised. Instead, newsletters featured customer stories in an effort to connect emotionally with users. This is not to say that the marketing team’s tactic wasn’t effective, but because both teams failed to coordinate, time and resources were wasted. The merchandising team’s effort was in vain.

The good news is that everyone is capable of seeing the company as one. We do this every day when we look at other companies.

For example, we don’t react to news on Google’s self-driving cars and say: “Wow, the marketing team on Google’s self-driving car project is really effective at …” Instead, we say: “Wow, Google is really catching a lot of eyeballs with their cars.”

Now we only have to see our own company as a unit.

Does my team see the company as one?


To help our team members see the company as one entity, we can perform a diagnosis of the company’s traits. This translates into the creation of a profile that defines our organization and exposes our group dynamics.

Having team members evaluate the organization as one re-enforces the mindset that we are all on the same boat, regardless of what teams we work with.

One approach is to survey all team members’ perception of the organization, asking the following questions:

  • What is your perception of our company’s current vision and strategy? How do we hope to impact the world, why, and how do we plan to achieve that?
  • What are natural tendencies and behaviors that you notice of your team, other teams, and the company as a whole? What are some biases that you observe, what do we enjoy/don’t enjoy doing, what mistakes do we repeat, and what do we prioritize and de-prioritize?
  • What frustrations do you experience that gets in the way of our company achieving its strategic goals? What are you repeatedly frustrated by?
  • What do you feel are our company’s strengths and weaknesses? What helps us achieve our goals and what drags the team back?
  • What values do we live by? Based actions and behavior observed, what values do you think we stand by?

Assembling a company profile based on every team member’s perception allows for the entire company to actively reflect on what type of animal it has become. This awareness alone will make team members more empathetic to other teams. Should we take it a step further and incentivize changes while praising improvements, teams will also implement changes to eliminate behaviors they perceive as negative or unproductive.

How often should we do this and why?

I recommend for this exercise to be performed at least twice a year for a couple reasons:

  1. Start-up companies tend to get distracted by new ideas that pull teams off alignment from the company strategy, so regular assessment helps to diagnose whether any team is going off-course, and to actively re-align them;
  2. Similarly, as a company evolves, its traits change. It’s thus important to regularly assess whether the company’s behavior is evolving in the direction that we want, creating the culture that we desire.

Let’s explore these two points in more detail.

1- Aligning teams to the company strategy

one team

In my opinion, it is easier for top leadership to set a competitive strategy than it is for them to keep all teams aligned to the strategy.

Especially at start-ups, individual teams tend to get distracted by new ideas and initiatives that fall outside of the company strategy. This is caused by a combination of factors including:

  • Ambitions and smart team members that want to change the world, but are easily distracted;
  • Ineffective communication from senior leadership about the actual strategy; and
  • Lackluster enforcement of the strategic plan.

The result is that actions across teams and individuals are misaligned and the company is pulled in all directions.

For example, a payment solution provider’s competitive strategy may be to focus on providing payment systems for large hotel management businesses, offering industry-specific solutions.

If that strategy is ineffectively communicated and ill-enforced, teams may take actions and decisions that are counter-productive. Marketing may run campaigns that attract all hotel operators, large and small, to get as many leads as possible. On the other hand, customer success may adopt a low cost strategy to boost profit margin rather than offering enterprise level support for clients.

The result will be that marketing money is wasted on attracting the attention of small and medium hotel companies we don’t want. And down the line, customer success will have a hard time retaining large clients without proper resources to create deep relationships.

Misaligned goals across an organization will thus slow down the company’s growth, if not reverse it.

To avoid such a fate, it’s critical to first decide and agree on a competitive strategy among the senior leadership team. Each department head should have a clear idea of their role as part of the strategy and who they need to collaborate with. Afterward, leaders will need to design and communicate the strategic plan to all their team members.

Results from the company profile survey will reveal whether everyone understands the strategy. Should there be confusion, misalignment, or lack of information on what team members believe the company strategy to be, we’ll need to clarify the strategy (i.e. highlight decisions and initiatives that are aligned or misaligned), actively refuse resources to misaligned initiatives, and review team goals for strategic alignment.

With limited resource, there’s no time to waste on misaligned initiatives.

Following up on our example above, the payment solution provider’s marketing goal should be to attract as many large hotel operators as leads as possible, and to neglect any small and medium size operators. On the other hand, customer success needs to provide enterprise level support with an appropriate budget.

2- Is the company maturing as desired?


Keeping an eye on the company’s behavioral tendencies, strengths, and weaknesses helps leaders acknowledge the company position, and whether we need to change course to stay relevant.

As teams gain experience tackling their problem, and as new individuals join the team, a company’s strengths will evolve and new skills will be added. On the other hand, a larger team will also bring new organizational challenges (e.g. bureaucracy, processes, politics) that may add to the company’s weaknesses and frustrations. Externally, competition and changing customer expectations will often redefine whether a company trait has become a new strength or a new weakness.

Blockbuster‘s rise and fall is a great example of a company that failed to understand itself, and its position within a rapidly changing market. With the introduction of Netflix type services and changing customer expectations, Blockbuster’s competitive advantage evaporated. What were once strengths (e.g. a lot of physical stores and access to customers) became weaknesses (e.g. too much overhead cost), while existing weaknesses grew in impact (e.g. limited stock and selection). Should they have acknowledged these market changes early, there was certainly a chance to stay relevant.

Since a start-up’s operating environment can change month-to-month, it’s critical that we regularly evaluate its evolution and position within the market.

Are we too optimistic?


It takes a healthy dose of self-belief, courage, and optimism to found a start-up company. This positive outlook on the future is foundational to the culture of most start-up companies, shared by almost all team members that decide to join a start-up and forego a safe job.

I, for one, certainly believe in my company’s eventual success, even though we’ve yet to make $1 of profit.

Fact is, a positive mindset is necessary to pursue dreams and work on unproven solutions. If we had any doubt in our success, we wouldn’t be pursuing this venture. We know that the odds are stacked against us, and yet, we decide to put up a good fight.

The upside of having an optimistic mindset is clear: We always have the energy to get back up after experiencing failure, and keep moving forward.

Yet, there is also a danger to our optimism: It can make us blind to our weaknesses. At start-ups, we have a tendency to turn a blind eye to our company’s structural problems, strategic threats, and other long-term issues. These issues tend to be ones that we can’t solve right away and necessitate company-wide collaboration. And because there’s always more urgent short-term issues to solve at a start-up, we tend to ignore our long-term challenges. With time, the team learns to turn a blind eye to structural problems and let their optimism take over.

What’s the result? Blind optimism can cloud the evaluation of a company’s true situation. And slowly, it can become culturally unacceptable to voice negative thoughts. Team members may not raise or report their frustrations and challenges, for fear of being perceived as pessimists or even worse, not believing in the company’s future success. Complaints and frustrations will often follow with someone saying “Yeah, but we work with really smart people. We’ll figure it out.” Like that adds any value to the conversation…

The leadership team is certainly not immune to blind optimism (they need it most!), so they may become unreceptive to team members’ concerns, shielded by ego and by the fear that there’s nothing they can do about the issue.

At that point, the entire company is no longer capable of objectively assessing itself. Everyone drank the cool-aid. As it is no longer looking to improve itself, the company will slowly become unable to face changing market forces, to resolve internal challenges, and ultimately, to hit its goals.

So allow me to share a word of advice: When assessing the company’s profile, ask team members to be brutally honest. In the wise words of my yoga teacher: “Observe differences, don’t judge.”

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

What we should never say to a new hire

What we should never say to a new hire

A relatively new team member (let’s call her Taylor) caught me out of the blue and said “Hey Blake, thank you.”

For what?” I asked Taylor, with a confused face.

For telling me that you don’t expect anything of me on my first day.”

Turns out, Taylor was at a leadership conference and one of the sessions focused on imposter syndrome. The session described how feeling like an imposter starts when we perceive what is expected of us to be more than what we think we can deliver. For example, we may feel like an imposter when we’re expected to cook Thanksgiving dinner when we can barely make a salad.

By communicating that I expected nothing from Taylor on day one, it eliminated any potential for imposter syndrome to develop. In turn, most team members are quite confident in their roles.

I wasn’t always this clear with new team members. Quite the opposite actually. I used to get so excited about finding someone that was a good fit that I expected them to solve all my problems right away. It didn’t help that we hired really smart, hard working, and ambitious people.

I’d often delegate work that required knowledge that nobody outside the company would have, and a lot of it. I would also fail to clarify whether they should be getting help on certain topics. New team members would then spend many more hours than veterans in the office, trying to make sense of the tasks by themselves. They thought that they were expected to do everything on their own, and that this was a test of their abilities. Most were too intimidated to ask questions.

While all team members successfully ramped up by themselves (speaks to their intellect and resilience), it wasn’t without stress. In 360 reviews, team members would communicate that I was demanding, intimidating, and impatient. Not traits that I want to be associated with when I’m trying to build long-lasting, transparent, and trusting relationships.

My goal has always been to create an environment where people feel comfortable asking questions and sharing their thoughts, so this was definitely a problem. What led to this?

In retrospect, these feelings likely started to develop from things I’d say to team members in their early days on the job, such as:

  • I saw that you’re working on a request for client X. They’re really important to us. I know that you will wow them.
  • So and so is dealing with a pretty tough request, can you help them since you have experience in Y?
  • I can’t wait to see the results from your work on project Z tomorrow. A lot of people are waiting on it.

What do these sayings have in common? They assume that the individual can independently complete the task with flying colors, and set the expectation that they are fully responsible for its success. Wouldn’t anyone be intimidated by these words, let alone new hires?

Fact is, even if new team members have performed similar tasks before, they’re now in a new organization that requires new knowledge and skills. Every workplace have unique processes, culture, and people that make them different from other workplaces. It’s thus unreasonable to expect anyone to be able to run at full speed without a ramp up period.

Let’s also remember that for some people, it’s their first time working with a start-up team. It’s their first time coping with an unstructured and chaotic environment. It’s thus our job as leaders to ease them into it.

The only thing we can expect of new team members is for them to ask a ton of questions. We need them to avoid making assumptions, and to never fear speaking up.

Based on the questions asked, and the speed at which they learn the job, it also gives us an opportunity to diagnose the type of coaching that they need.

So instead of saying “I know that you have experience with X, can you help…,” it’s much more fair to simply ask “What’s your experience with X? Could you tell me more about it?”

What does success look like? Success translates into a new hire that has the confidence to attack challenges we throw at them without feeling like an imposter. They should know that as a team, we help each other and face challenges together.

I don’t expect anything from you, except that you ask a ton of questions.

Related reading: Presence: Bringing Your Boldest Self to Your Biggest Challenges

Recommended exercise

Let’s include a new step on orientation checklist for new hires: Communicate that we expect nothing from them, simply that they become the best students ever and ask a ton of questions.

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

A system oriented approach to hiring

A system oriented approach to hiring

First, a personal story.

After we raised a series B at our start-up, we began to rapidly scale and hire new team members. On my team alone, I was looking to hire three additional technical team members to support our growth targets. I started to review dozens of resumes a day and spend half my days phone interviewing.

Our hiring process was time consuming to say the least. To increase efficiency, we would make changes to the process based on what we learned every week. However, we ended up adding new steps and questions, which morphed our hiring process into a monster. For fear of letting the wrong person join the team and wasting people’s time at an in-person interview, we over-assessed candidates.

We treated recruiting as a sales funnel that had to be optimized.

The result was that it took weeks for a candidate to make it thru to the final round, during which they had no idea of the overall process. At in-person interviews, we started to ask so many technical questions that some of them began to be unrelated the role itself. Surely, negative reviews began to pop up on about our inefficient and unfair interview process. A revamp was needed.

We thus got together with our company recruiter and started to create a process from scratch. Our goals were to find a fitting candidate using the least resources possible, keep candidates excited about the prospect of working with us throughout the progress, and use data to optimize. We therefore started to A/B test interview questions, assessing for their effectiveness at revealing if a candidate was a fit for the role, as well as experimenting with more/less touch points to assess their impact on whether more/less qualified candidates made it through the funnel. We treated recruiting as a sales funnel that had to be optimized.

The result was less time spent on hiring and more qualified candidates making it through the funnel. And those that came in were always excited to speak with us, praising us for making the process transparent and fun.

In this blog post, I’m going to share a hiring process that has worked effectively in assessing and hiring technical people. My hope is that it helps fellow leaders reflect on their own hiring process and:

  • Sell the job and the company to superstars;
  • Ensure that candidates can do the job before being hired;
  • Assess whether the candidate will fit into the company culture;
  • Find the right candidate in less time; and
  • Establish a process that can be evaluated and improved upon.

In my experience leading start-up teams, hiring the right or wrong person can make or break the company. A superstar can inspire an entire company to set higher goals, whereas a mediocre hire will bring frustration to all. My opinion is often shared by VCs, whom don’t just invest in a company with good products and services, but also in a strong team. That includes Warren Buffet, who prefers to invest in companies with a strong management team.

How do I systematically interview candidates?

people funnel

It’s a good idea to approach hiring like we approach sales, thinking of it in terms of a funnel process. Doing so forces us to establish a process that can be consistently executed by different people, measured for effectiveness, and improved upon.

In the following sections, I will be exposing a hiring process that I’ve used to assess candidates for technical roles. I will explain what I’m assessing for at each step, along with why it’s a relevant step. This is meant to help think of hiring as a process rather than an ad-hoc task.

There are 8 steps in my hiring funnel. They will take us from screening resumes to making an offer. Let’s explore this in detail.

1. Reviewing resumes: Is this person qualified?

At this initial stage, our goal is to filter out candidates who clearly do not have the skills necessary to perform the job, or that clearly have no interest in the position. It’s difficult to clearly assess anyone based on paper resumes alone, so we’re simply on the lookout for clear signs of misfit, including:

  • Experiences and skills that are completely misaligned with the role and position e.g. If a candidate is applying for an electrical engineering position, yet has 10 years of experience practicing medicine and no engineering related work or education, it’s probably not a good fit.
  • Cover letters and resumes addressed to the wrong company e.g. If a candidate refers to a competitor or a different company in the cover letter sent to us, it’s not only a sign that they are not detail oriented, but also that they don’t have a special interest in our company. In the hyper-competitive world of start-ups, there’s no room for individuals that don’t have a strong interest and commitment to our company.

My recommendation is to let candidates with even a slight chance of fit to pass this round. In our world where art majors can be genius robot engineers, it is extremely difficult to say with confidence that someone is a misfit based on paper resumes.

OUTCOME: All candidates that clearly cannot perform the job are filtered out. At this stage, having ~50% of candidates that applied pass the round is acceptable.

2. Phone screening candidates: Do they fit our basic needs?

phone happy

Once we have a preliminary shortlist of candidates, it’s time to call them up and schedule a quick 15 or 30 minutes phone interview. Our goal is to ensure that candidates understand the role, assess for basic fit, and for us to sell the company culture by introducing a person into the process (most companies fail to introduce themselves until later). It is not yet time to assess for technical capabilities.

Considering that there is nothing technical about the call, I recommend for a Human Resource team member to execute this step and save the hiring manager some time. The interviewer should:

  • Introduce the company and speak to its history: Describe the company’s mission, core values, and general culture.
  • Once there is clarity on what the company does, ask the individual how they’d like to ideally contribute, or what role they’d like to ideally take on. We’re checking whether the candidate is familiar with the job description and whether they truly have an interest in the listed position.
  • After the candidate has shared thoughts on what they’d like to do at the company, describe the actual position’s responsibilities, day-to-day work flow, and challenges faced. This helps clarify what the person is actually applying for.
  • At this point, we have a clear picture of what the candidate is interested in doing, and the candidate has a clear picture of the opportunity offered. If there is alignment, commend them on doing thorough research on the role. If there is misalignment, highlight that fact and ask if they’d like to apply for a role that matches their interest closer. Should they say yes, then we need to come to an agreement to either pass on this role, or still pursue it as a “foot in the door” position that the candidate will likely grow out of.
  • Assuming that a person understands the role and wants to pursue it, let’s next ask about their expected compensation. Here, we’re assessing whether expectations match what we can offer, and give both parties an opportunity to get on the same page. If their expectations are within our budget, we don’t need to discuss more details at this point. Yet if an individual is asking for a salary that is 30% higher than the budget, it’s time to set the expectations straight and ask if they’d still like to continue the process. That’s only fair. If a candidate decides to not pursue the opportunity for salary reasons, consider letting them go. Early stage start-ups should avoid hiring team members that put a high importance on salary and benefits; start-ups need people that believe in the vision, that want to make an impact, and that want to learn. Even if we have the money, I highly recommend to only hire team members at or below market rate to ensure that people are joining because they believe in the company mission and value the adventure rather than the money. We can always bump up their salary once they prove themselves on the job.
  • Once there is clarity on whether the person is interested in pursuing the role, and we confirmed that their salary and benefits needs fall within the position’s budget, take a decision on whether they should reach the next round live on the call. Should we decide to push them into the next round, let them know that the next step will involve some homework (see step 3). Explain that it is meant to expose them to some of the work involved on the job.

OUTCOME: All candidates beyond this point have a clear idea of the role they’re pursuing, including a general idea on the position’s salary and benefits. At this point in the process, we should have filtered out another 25%+ of candidates who either are not interested in the role, or have misaligned salary/benefit requirements.

3. Assign homework and tasks: Can they do the job?


The best way to see if an individual is qualified for a role is to have them do the job. While we may not be able to have the person work with the team for 2 weeks before taking a hiring decision, we can certainly assign them unclassified tasks and homework to test how they’d do on day-to-day tasks.

e.g. If we’re hiring a marketing director, ask them to design a plan to launch a new product or service. If we’re hiring a sales executive, have them call us to sell our own product back to us. If we’re hiring a data analyst, have them perform an actual analysis with sanitized data.

It’s critical that the work assignment or project is as close to what they’d be doing day-to-day as possible. It’s both an opportunity for candidates to experience work in this job, as well as a chance for us to evaluate a candidate’s work.

Therefore, homework assignments should be designed by the hiring team – they alone have the competency to design the tasks. Considering that most experienced candidates have a day job, I recommend to target a 1 to 2 hour completion time for the project so that they can complete it in one or two evenings. This means that anyone on the team should take less than an hour to complete the tasks themselves. A deadline should also be communicated to candidates to keep the funnel moving.

After the candidate submits their work, the hiring manager or a designated team member should be assigned to review task responses, and decide whether they’ve performed well enough to advance.

OUTCOME: All candidates that pass this round will have shown a real interest in the position, and proven their ability to fulfill the role’s basic technical requirements.

4. In-depth phone interview: Will the team like them?

phone interview

Now’s the time for the hiring manager to formally interview the candidate via phone and assess both their interest and their technical abilities. This is an important step as it is the last gate before candidates are brought in for in-person interviews – not properly assessing a candidate’s abilities and fit at this stage can result in many hours of wasted time for the team.

Assuming that we’re hiring for a technical role, I recommend to structure the phone interview as such:

  1. 5 minutes: Introduce the role and ask for clarifying questions about the role. There needs to be absolutely clarity for the candidate as to what the position is about and what the day-to-day looks like.
  2. 15 minutes: Ask a ton of questions, from many different perspectives, to understand why the person is interested in this role, why they’re interested in our company, why they’re leaving their job, what they hope to learn, how they plan to grow, where they see the industry going, etc. This helps assess whether the person is truly interested.
  3. 15-20 minutes: Ask some basic technical questions to test an individual’s skills on the spot. These are questions that a person with the right technical experience or education can answer in a heartbeat. We’re essentially making sure that the individual didn’t have someone else do their assignment. e.g. If we’re hiring a digital marketing person, ask them about the core metrics that we need to monitor to accurately evaluate our online ads’ performance.
  4. 10-20 minutes: Ask them if they have questions. A prepared individual truly interested in our company will have many questions about the organization, the team, the culture, all relevant to their ability to perform on the job.

If an individual didn’t impress us on the phone one way or another, skip them. If we misjudged and skipped a candidate that was really passionate about the role, they’ll likely reach back out and ask for a second chance if they really want the job. A significant amount of time and resources is needed to properly interview individuals in-person (the next step), so only bring in individuals that impressed us. In a start-up environment, there is no room for mediocrity as it would drag the entire team down.

OUTCOME: Anyone that passes this critical round has impressed us in terms of both interest in the position and basic technical abilities.

5. In-person interview: Will they add value to the team?


In-person interviews are a chance for different team members to meet the candidate, and vice-versa. For this interview to be effective, there needs to be a high level of coordination to ensure that all conversations complement each other and don’t unintentionally overlap. Allow me to share some tips on this process:

  • Loop in anyone that will be impacted by the hire to interview: Beyond the direct manager, I recommend for a manager two levels up (a director or VP) to also participate in the interview to show that the leadership is invested in all team members. If the team size is small enough (4-5), all team members should also interview the candidate. If the team size is larger than 5 individuals, different people should take turn interviewing different candidates over time. Everyone should take part in the interview process as it allows different assessment perspectives to be shared, on top of catalyzing ideas on how to improve the hiring process.
  • Decide on a set of traits to assess for: Depending on the role, there is likely a specific set of abilities that we need to assess for. Together with all interviewers, I recommend an agreement as to what these skills and abilities are. Especially for first-time interviewers, or for new roles, this is not always clear. This will help everyone evaluate a candidate effectively. e.g. For a sales engineer role, we may need the candidate to 1) be an excellent communicator; 2) know at least one sales system ; 3) have technical experience on …
  • Collaborate on the group interview: With multiple individuals interviewing, we can cover much more ground by having each person assess for a different skill set. For example, we may have one person assess for cultural fit, another assess for technical abilities, while another person assess their communication skills. At the same time, there are also aspects and questions that should be assessed by everyone: If an element is so important that we cannot take the chance of misjudging, have multiple people assess from different perspectives.  The goal here is to ensure that a candidate’s story or ability is consistent throughout the interview.
  • Document and share interview questions that everyone plans to ask in one file: Once everyone knows what they’re going to ask, put it all together in one file to ensure that all topics complement each other as desired. Interview questions also need to flow – the order in which questions are asked matters. The toughest, most technical questions, should go in the middle of the interview, after the person has warmed up to questions, and before we make sure they leave on a good note.
  • Sell the job: Top candidates are likely to receive multiple offers and have choice. It’s thus critical that we sell the job during live interviews. This translates into:
    • Avoid having 2 or more interviewers in the room at the same time. It’s too intimidating. If more than two people need to interview, split into multiple sessions.
    • Ensuring that everyone’s body language is respectful and enthusiastic.
    • Making sure that the interview room is clean and allows for a constructive, non-threatening conversation: Avoid sitting across from the candidate – sit in a circle instead.
    • Being upfront as to what will happen during the interview. If we’re going to ask tough logic questions that don’t have clear answers, let them know before we ask it. Avoid putting them on the spot unnecessarily.
    • If the interview lasts a long time, offering water, snacks, and breaks. Make them comfortable and relaxed.
    • Describing the benefits of working here along with the best parts of the job. There are many opportunities to expose the benefits of our work environment throughout the interview. e.g. Let’s say that we ask what a person wants to learn on the job. We can follow up on their answer with: “That’s really great. At our company, we put a lot of emphasis on personal development. We encourage team members to take at least 4 hours a week to spend on personal projects, in addition to giving you a budget of X per month for training.”

What to avoid: Avoid asking questions that simply fill up time and don’t assess a person’s ability to do the job or their interest in the role. This includes logic questions and puzzles that don’t assess the technical abilities necessary for the job, but simply intimidates the candidate.

OUTCOME: A candidate has a chance to meet and speak with different team members, and we get to assess a candidate on all aspects important to the role.

6. Taking the decision: Do we agree that they will add value?

yes or no

Decisions are easy when everyone either likes or dislikes a candidate, but can be quite difficult when there are mixed feelings. Allow me to share a process that will help everyone come to an agreement:

  1. Right after the interview session, send out a questionnaire that asks each interviewer to:
    • Assess the candidate on the agreed upon set of traits (I recommend a binary choice of 0 and 1: 0 = the candidate failed to demonstrate this specific ability; 1 = this candidate succeeded in demonstrating this ability). Avoiding a middle option gets rid of ambiguity.
    • Decide whether they are in favor or not in favor of hiring the candidate. Again, avoid ambiguity by asking for a yes or no answer.
    • Ask for details surrounding their responses above.
  2. The hiring lead or an HR person will then review all responses to assess whether there is:
    • An agreement from the majority of interviewers to hire the individual, or not hire the individual. If this is the case, the decision is quite straight forward; or
    • There is disagreements among many individuals and mixed feelings as to whether we should hire or not hire the candidate.
  3. If there is disagreement, it’s important to discuss in detail everyone’s perception of the candidate’s strengths and weaknesses. For interviewers that are still not comfortable hiring the candidate after a discussion, we need to see whether there is a way to address their concerns in a follow up interview or exercise. e.g. A candidate that failed to demonstrate their technical abilities may get a second homework assignment and follow up interview to respond to some technical questions.
    • If there is little that we can do to ever become comfortable hiring this candidate, then pass;
    • If there is a chance that an individual may succeed in a follow up interview, then have the unconvinced interviewers lead it. They can report back on whether their concerns have been addressed (hire), or if they are still not comfortable (pass).
  4. A final note of caution: Most candidates interviewed will have flaws and weaknesses. That’s normal. Nobody is perfect. However, before hiring an individual, it’s important to assess whether our organization is OK with these weaknesses, or if we have the resources available to coach and mentor the individual. e.g. If a sales engineer candidate is well versed in our sales system and technically competent, yet has confidence issues when communicating, we need to decide whether we have the resources and time to help the individual understand their insecurities and gain some confidence.

OUTCOME: At this point, there is a clear decision on whether we will extend a job offer to the candidate.

7. Giving the offer: How can I guarantee their acceptance?


When possible, I recommend for someone else than the hiring manager to give the offer. This ensures that any negotiation that happens with regard to salary and benefits is carried out fairly, and doesn’t taint the relationship between a hiring manager and the new hire.

It’s very likely that when an offer is made, all kinds of weird requests come in. Some will have already scheduled four weeks of vacation, while others will want double the pay. This is when negotiation starts. It’s important to avoid taking any decisions on the spot. I strongly recommend to loop in a seasoned negotiator for advice or at least read this book. In a constructive negotiation, both parties try to understand each others’ priorities and means. To fulfill our goal of starting a long-term relationship on the right footing, we need to ask as many questions as possible to understand why the individual is making their requests, and also explain the basis for our offer. There is usually a way to satisfy both parties’ core needs creatively.

OUTCOME: A strong offer will have been made that satisfies both the candidate’s requirements and our needs. Let’s remember that our goal here is to both close the deal and start a new relationship on a strong footing. Should the candidate accept the offer, it’s also time to start the new team member’s profile. This is the start of their growth path at the organization.

8. Improve with data: How do I make my hiring funnel more effective?


Obviously, our hiring funnel won’t be at its best on day one. It’s thus a good idea to regularly review the interview process, and see if each step is as effective as it can be. Effectiveness can be assessed by looking at how candidates that passed a specific step fared on the next step(s). Should any steps be ineffective, we can try different approaches and ways to achieve the same goal. Here are some questions we can ask ourselves to assess the effectiveness of each funnel step:

  1. Reviewing resumes: Are there enough candidates in the pool of applicants? Are we letting through too many or too few candidates? Based on candidates that performed well on phone screenings and task responses, do we have a better idea of the ideal candidate profile? What do the resumes of high performing hires look like?
  2. Phone screening candidates: Do our questions effectively assess an individual’s interest in the role? Are we clear in communicating what are the role’s responsibilities?
  3. Assigning tasks: Do our tasks fairly represent the day-to-day work? Are our tasks effectively assessing a person’s technical abilities? Are too few people responding to the assignment? Who tends to drop out of the process here?
  4. Phone interviewing: What percentage of candidates pass the phone interview stage, yet fail the in-person interview? What profiles of people tend to pass the phone interview, but fail the in-person one? Do too many/too few people answer the technical questions correctly?
  5. Interviewing in-person: Do all interviewers know what to assess a candidate for? Do most candidates seem at ease or seem intimidated? Is a certain trait that we’re trying to evaluate difficult to assess? Do our questions cover all areas we want to assess? Based on hiring decisions of previous candidates, are we bringing in the right people?
  6. Taking the decision: Is the interview team mostly in agreement, or do they tend to debate more often than not? Is there a specific trait or performance area that is most debated? Are we asking the right questions during the interview? Have recent hires proven their abilities?
  7. Giving the offer: What percentage of people accept our offers? Why do certain people not accept our offers? What do people mostly negotiate on? What challenges do we face in closing the deal?

I recommend for a specific team member to manage the hiring funnel and lead any process improvements. This can be either the hiring lead, a team member, or a HR representative. The goal is to maximize the effectiveness of the process, to improve the odds of hiring the next superstar.

If you’re interested in reading more about hiring, here are a couple more resources:

Recommended exercise

Let’s ask our new hires: “What questions or processes did you find irrelevant during the interview process?”

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start⬆Mngr handbook pt. 3: Leadership and coaching go hand in hand

start⬆Mngr handbook pt. 3: Leadership and coaching go hand in hand

First, a personal story.

Taylor (fake name) joined my team after spending years as a technology consultant with a big tech company. As a team member with experience working on large projects, I let the Taylor lead an important innovation project on top of Taylor’s day-to-day duties. My assumption was that Taylor had some experience with project management, so could hit the ground running. Therefore, I simply set the goal for the project, clarified what we needed as deliverables, and let Taylor run with it.

After a few weeks, I heard no news of the project, so I actively inquired about the status with Taylor. He responded: “Yup, everything’s fine and I’m on top of it.” Another few weeks passed and I started to notice that milestones were missed and we were running behind schedule. I checked in with Taylor again, and we discussed what was happening. Turns out, our initial timeline was too aggressive and we had other urgent fires to fight, so the project was de-prioritized. “OK…” I said, feeling somewhat disappointed that I had to reach out to hear this. I expected this type of news to come to me. However, I let it go. My thought was that Taylor simply has a different project management style than me and had things under control.

It was unreasonable on my part to expect Taylor to be able to lead the project independently

The good news is that the project was eventually completed. The bad news is that it was completed weeks past the initial deadline, and the end result did not meet our initial expectations. Needless to say, I was not very happy with the way Taylor managed the whole project – not so much that it failed to meet initial expectations and timelines, but that I had no clue on what was happening throughout the process. What kind of project management was that?

During a one-on-one with Taylor, I brought up my disappointment with the way the project was managed, and asked why I was kept out of the loop. To my surprise, I learned that Taylor had no idea that I needed to be briefed. He assumed that as project lead, nobody else needed to be bothered with status updates. This baffled me. I was the project sponsor, an important stakeholder, and yet this project manager didn’t think that I needed to be briefed on progress. You can imagine how upset I was.

At this point, I couldn’t help but ask Taylor: “What projects have you managed where the stakeholder didn’t care about status updates?”

Taylor said: “I’m not sure. This is the first time I’ve led an entire project. In the past, I’ve only helped to coordinate the change management side of projects.”

How foolish I felt. Here I was, thinking that Taylor was able to lead a project, having had experience project managing large IT projects. Yet my assumption was wrong. It was unreasonable on my part to expect Taylor to be able to lead the project independently without any assistance. It was even more unreasonable for me to expect the project to be managed a certain way without ever communicating these expectations first.

So what did I learn? Never to make assumptions about a person’s abilities. If we have assumptions, we need to assess and validate them. The alternative is unreasonable to both the team member and ourselves: The team member ends up with unreasonable expectations that they can never meet, and we are guaranteed to be disappointed. The reality is that most team members need some support and coaching before they can run on their own. In other words, to be effective leaders, we need to be effective coaches.

So let’s make sure our team members have what it takes to succeed and meet our expectations. In part three, we’ll explore critical leadership concepts that will help us:

  • Coach team members;
  • Delegate and share responsibility; and
  • Ensure that team members meet our expectations.

What are some great reads on coaching?

Why is coaching so important at startups?

At start-up companies, leaders can’t just set a vision and delegate. With limited resources, we often work with ambitious, extremely smart, yet inexperienced team members that don’t always have the  skills necessary to carry out their tasks. Young team members tend to not have the project management, communication, or even technical skills necessary to succeed in their roles. That’s where we fill the gap and help them grow.

At one end of the spectrum, team members need to learn something completely new from scratch, and at the other end of the spectrum, team members can be so proficient that we only need to set a goal and delegate a responsibility entirely. Reality is that most team members will be somewhere in between these two extremes with regard to a certain skill.

As leaders, I believe that it’s our duty to help individuals grow toward mastery, setting the expectation that we want them to one day take ownership of certain responsibilities entirely. To achieve this, we need to coach.

At its core, a good coach first analyzes the current abilities of a team member to gauge what type of leadership the individual needs with a specific task or skill (e.g. direction, coaching, support, or delegation). Once we know what the individual needs, we will adopt the relevant approach, communicate our intentions and expectations to the team member, and work together to advance toward delegation.

The rest of this blog will expose tips and insights that will help us throughout this process.

How do I coach?

We’re going to take a page from the Putting the one minute manager to work to remind ourselves of how to train team members on new skills:

  1. Tell (what to do)
  2. Show (how to do)
  3. LET the person TRY
  4. Observe performance
  5. Praise progress or Redirect

As practical advice, reprimands should not be given until a person has proven that they can successfully achieve the desired task. Reprimands are reserved for situations where an individual failed to achieve something they are capable of. When teaching a new skill, we need to focus on coaching and praising what they’ve done right. Reprimanding a team member before they experience success is unreasonable and will de-motivate the team member in the process.

What if I don’t have the knowledge to coach a specific skill?


As leaders, we are responsible for setting a vision. This responsibility however does not always translate into knowing how to achieve the vision, nor into the ability to mentor team members on how to achieve the vision.

The one-minute manager system assumes that leaders have the skills to train an individual, to provide direction, coaching, and support. Yet that’s not always the case in real life.

For example, a Chief Financial Officer may have a developer as direct report to help build software applications that facilitate financial forecasts and reporting. Yet it’s unreasonable to expect the CFO to be able to train or mentor the developer and help grow their technical skill set.

In such scenarios, when we are not the best to train a direct report, external help needs to be leveraged: There may be someone from another team or someone from outside the company that is better positioned to coach. Should there be a lack of mentors at the organization, an individual can also rely on books and educational courses to learn independently. However, nothing replaces an experienced human mentor.

Independent of how training is performed, it’s important to set clear expectations with team members as to whether the direct manager or another person will be mentoring them. A team member may also need multiple mentors should they require different skill sets.

If an organization lacks mentors for junior team members, there is only one choice: Hire more experienced individuals. This is especially important when training and coaching new managers, whom we depend on to set and communicate expectations, in addition to keeping goals aligned between teams. In an ideal scenario, there should be at least one management mentor for one or two first-time managers, and one technical mentor for every three or four junior individual contributor. Yet this ratio is rarely met at early stage start-ups: They usually want to save on salary cost and hire smart yet inexperienced individuals straight from school. That’s a mistake.

Having too many junior managers means that the organization learns and grows by trial and error. This behavior lengthens the time required to identify a clear company strategy, develop effective and efficient processes, and slows the pace of growth. For most start-ups, there is limited time to achieve critical goals, so there needs to be a healthy ratio of experienced mentors to first-time managers.

In my experience, the most effective mentors have worked at different organizations or industries that have faced similar challenges. This enhances their ability to help junior managers gain new perspectives, think outside the box, and at the very basic level, teach the overall role of a leader.

If hiring experienced managers is a luxury that our start-up can afford (yay!), there is one additional caveat to consider: Not all experience is the same.

Let’s assume that we’re a 50 people start-up with $2M annual revenue, wanting to grow to 200 people and $20M annual revenue, and we’re looking for a new sales leader to help us get there. The logical solution is to find sales leaders working at similar companies that have achieved $20M in annual revenue. However, we need to acknowledge that not all leaders in those positions will have the relevant experience to help us.

For example, a sales leader at the ~20M annual revenue company may have started their career when their company had already achieved ~15M in annual revenue. This indicatesthey have the experience of working in an organization that we want to eventually become, but maybe not the experience to help us get there. They achieved success with a support system of a company that’s doing $15M a year, not with a system that’s currently doing $2M a year. They may be completely lost working with a smaller budget, team, and different culture.

So when choosing an experienced leader, the ideal scenario is to find someone that is not only in a position that we want to achieve, but that has also worked to grow their organization from a position similar to our position today. This means that the individual has already made the mistakes that we foresee making, and has gained relevant insights on how to tackle these challenges better.

What do I delegate?


It’s a good idea to regularly assess if there are responsibilities that we can delegate and transfer/share ownership on. This ensures that team members get new growth opportunities and that we keep an optimized workflow. Here’s a simple exercise that has helped me identify what to delegate:

  1. List all the responsibility that I currently have, and all the items on the to-do list and backlog.
  2. Next, ask myself “What unique value do I add to each task?”

If I truly add a unique value to a given task or responsibility, then I keep it. If we are not sure, asking some additional questions can help:

  • Am I the best person to perform this task or responsibility? If we are not the most skilled individual to perform this, or if someone else can dedicate more energy to achieving it better, we should work toward delegating it.
  • Am I positioned to maximize the impact of this task or can someone else have the same or even greater impact? Let’s compare two tasks: Give a lesson on time management to all team members; and advising one specific team member on time management. In the context of maximizing impact, giving a lesson to the group impacts a much greater number of individuals than advising one specific person, so the lesson is more important to focus on. The question then becomes whether we are best positioned to do that, or if someone else can do the job better and/or impact an even greater number of people.
  • Am I complaining that I never get to perform a certain responsibility because I’m always bogged down by another one? Then it’s time to assess which responsibility has a higher priority, whether they are both valuable to the team mission, and who is the best person to carry either of them out. Assuming that both responsibilities are critical to the team’s mission, work toward delegating away one or both responsibilities should another individual be better positioned to execute. Continuously not having the time to perform a responsibility is often a strong indication that there is an opportunity to delegate.
  • Am I constantly catching up on day-to-day work and not strategically planning the next steps for the team? As leaders, our core responsibilities is to plan for the future, to think of more effective and efficient ways to achieve our team mission and company goals. To that effect, it’s important to regularly allocate time for strategic planning. If we don’t have the time to do that, there is likely an opportunity to delegate away some of our day-to-day, non-planning work.
  • Do I enjoy doing it? Do I enjoy a task so much that my day would become too miserable should I delegate it?

It’s normal to feel anxious delegating certain tasks we hold dear, thinking that others may not know what to do right away. That’s normal. That’s why a leader needs to start with a directive approach, and work toward coaching and supporting team members. A leader also needs to expect team members to make stretch mistakes when doing things for the first time. It’s a sign of progress.

Who do I delegate to?

A contractor is on a mission to build a house. He assigns floor work to a carpenter and sink installation work to a plumber. Logical, right?

Similar to the foreman, it is a good idea to delegate work to individuals based on their expertise, skills, in addition to their interests and personal goals.

Delegate thoughtfully and team members will reward their leader with trust and loyalty. Delegate blindly and team members will hate their jobs. To help assess what to delegate to whom, here are some questions I ask:

  • What motivates the team member?
  • What is that individual’s strength and weaknesses?
  • Does the task match the person’s interest and strengths?
  • Does that person have the appropriate resources? Including time and tools.

To help team members grow, it’s a good idea to continuously experiment and expand the scope of responsibilities to delegate. This allows team members to prove themselves little by little, and taste success along the way. A thoughtful leader will first delegate something that a team member will  surely succeed in, then move toward bigger responsibilities where they need more time to learn and master.

Of course, there will be times when we need to delegate a task that nobody is interested in. For example, we may require a data scientist to perform a data entry task. In those circumstances, it helps to communicate why the task is important – this gives the individual purpose, even if it doesn’t add to the individual’s long-term goals and motivations. Of course, doing this repeatedly runs the risk of diminishing an individual’s overall interest for their work.

Recommended reading

Who am I?

To help adopt the principles of the One-Minute Manager system, let’s take a step back and look at ourselves in the mirror. The more self-aware we are, the more effective we will be at identifying the appropriate approach to adopt when interacting with team members. To help get started on the journey to self-awareness, allow me to share a couple personality tests below:

How does self-awareness make us better leaders? It starts from leveraging one’s strengths to add a unique value to the team, and more importantly, acknowledging one’s weaknesses to not let them get in the way of doing a good job. For example:

  • A manager with a commanding personality may enjoy delegating and be an effective macro-manager, but they will need to make sure to not forget coaching and supporting new players before they can be expected to run on their own.
  • A introverted manager may need to make an extra effort to connect socially with their team (e.g. have lunch with the team), and commit time to observe their team members’ behavior and praise or reprimand accordingly.
  • A flexible manager will need to learn to be authoritative and strict when delivering specific, non-arguable reprimands.

How do others lead?

I’ve assembled below some additional resources on management and leadership. It’s a good idea to tie back any learnings from these resources to a management system like OMM. This helps us understand why OMM tactics work, and also allows us to build skills and knowledge on top of its basic foundation.

Recommended exercise

Let’s ask ourselves: “Have I been disappointed by the performance of a team member lately? If so, have they had the necessary coaching to actually succeed? Were they ready to take on that challenge independently?”

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start⬆Mngr handbook pt. 2: How to set clear expectations and motivate the team

start⬆Mngr handbook pt. 2: How to set clear expectations and motivate the team

First, a personal story…

On an ordinary afternoon, an A-player, superstar, technical genius on the team (let’s call her Casey), sent me an impromptu same-day meeting invite. I’ve always been suspicious of meetings without pretext. My guess was that Casey needed my help with something urgent, or wanted to communicate something special. In either case, it’s my philosophy was to deal with such situations sooner rather than later, so I simply walked over to the Casey’s desk and asked if they wanted to sync up right away.  She agreed.

Right after we settled into a meeting room, Casey told me that they had taken up a job at another organization.

This wasn’t a total surprise, as Casey had asked for a raise a few weeks earlier, which I declined (we have a company policy to discuss compensation annually, ensuring consistency for all team members). I went ahead and congratulated Casey on their career move, and out of curiosity, asked if they would have stayed on if the desired salary increase was given. Casey answered: “Maybe, but it would only have delayed my departure. I’m kind of glad I didn’t get it.”

I realized that I had failed to set clear expectations with the individual

That response puzzled me. Casey wasn’t leaving just because of pay (my initial assumption), but rather because they were unhappy with their job. How could this be? I had a trusting relationship with Casey, held regular one-on-one meetings, and had an ongoing professional development conversation, where we’d discuss her interests and try to find project opportunities that aligned with those. Aside from the salary issue, everything else seemed fine.

Why was this outstanding team member unhappy?

I got part of the answer by further chatting with Casey and reading her exit interview: Among smaller frustrations, Casey had no clear sense of what was expected, what success meant, and in turn, always felt unaccomplished. Interesting… I thought.

The question then begs… How could someone so successful, that I always praised feel that way? At every meeting, I only had good things to say: “I’m really happy with your performance”, “You’re rocking it”, “It’s a pleasure to be working with you.”

For weeks, I was trying to figure out how Casey could have felt unsuccessful. I then got another piece of the puzzle while randomly chatting with a colleague, a friend of Casey’s at the office:

“Casey was unhappy because there was always unfinished work at the end of the day, which she would continue at home, often disrupting her family life. She didn’t know when it was OK to stop. At the same time, Casey never really knew how well she were performing. Every time that you’d say “good job,” it added to the confusion and nuance: Casey simply didn’t understand what she had done that was so good.”

At the time, I didn’t really know what to make of this insight. But skipping ahead a few weeks, after discussing this with my leadership coach, I realized that I had failed to set clear expectations with the individual, failed to design a personal growth plan, and failed to be specific in my praising. The team member was going above and beyond relative to my expectations, but I failed to ever communicate what these expectations were. I’m not even sure if I truly had any expectations beyond working hard and doing their best. This left Casey constantly guessing about whether she was successful. And as most top performer in such a situation, Casey simply did more and more, better and better, without a clear goal. Over time, this likely drained her.

Upon further reflection, I realized that over years of formal education and examination, society has trained many of us, especially STEM students, to expect leaders to set clear goals and define success for us. We gauge our performance and areas to improve from report cards. We’ve rarely had to define success and set expectations by ourselves. So when we land a job where performance isn’t as clearly communicated as in a report card,  we feel lost. High performers that strive to beat expectations and earn A+ marks may not know how to interpret nuanced feedback, or gauge their performance independently. This is especially true for people straight out of school, and for jobs at start-ups where the definitions of success isn’t always clearly defined, and changes often over time.

It was my job as a leader to set personal expectations and goals for team members, and to help them continue their development. Even a simple expectation around timeline for projects or tasks would have helped the person understand what success looks like. Leaving people to independently figure out their success criteria may be asking too much if the individual has never done it. It’s a skill that needs to be learned. In short, I failed as a leader to set clear goals.

So let’s explore how to help team members define success and avoid confusion.

In part two, we’re going to discuss the basics of leadership. We’ll introduce a management system to help us maintain consistency in our interactions with team members, and explore important resources to help us:

  • Communicate clear expectations to team members;
  • Help team members meet expectations;
  • Track team member progress; and
  • Share constructive feedback.

What are some great reads on leadership?

The following two books provide a solid introduction on how to properly set expectations. I managed people for two years before being exposed these concepts, and certainly regret not having had this knowledge on day one. It’d have save my team and myself a lot of frustrations. They each take 45min to read, so we really have no excuse to skip them.

  • The One Minute Manager: The one minute manager (OMM) is a great basic management system that I recommend adopting. Having  a system in place helps us be consistent in our interactions. I’ve found the following concepts particularly handy:
    • Agreeing on expectations and goals early
    • Praising and reinforcing desired behavior and actions with specificity
    • Reprimanding if individual failed to achieve a desired behavior they have successfully achieved previously with specificity
  • Putting the One Minute Manager to Work: This one helps us implement the concepts explored in the OMM. While not as mind-blowing, I’m of the belief that success comes down to execution. And this book helps execute. What I personally found useful include:
    • 5 steps for training a learner to become a good performer
    • PRICE system

Beyond this point, I will assume that all readers have acknowledged the concepts introduced in the above readings.

How do I implement a management system?

The table below shows an example of how we can use the OMM’s PRICE system to plan and set goals.

In the context of management, the most used categories of goals includeproject goals (e.g. design a new feature / build a house), team or organizational goals (e.g. hit sales target, keep retention at x%), and individual performance goals (e.g. ability to query in SQL, ability to manage time independently). All three types of goals can benefit from the PRICE system as a way to agree on the specifics and keep track of our progress.

PRICE System Step Pinpoint + Record Involve Coach + Evaluate
Details of … Project goal OR Team goal OR Individual goal What are your expectations? Why?
What is the measure of success / performance?
What is your plan on sharing these expectations with the team member? What will you be looking to praise? When/how will you dedicate time / find time to praise? What will you be looking to reprimand and avoid? When will you dedicate time to reprimand?
EXAMPLE TEAM GOAL: Sales team goal Hit $50,000 in new monthly revenue to maintain growth at 25% over past quarter.

This translates into: 20 new leads per week per agent; $15,000 new revenue per week per agent.

Expose goal at beginning of month; showcase progress via email report weekly

Specifically, report on “% to goal completion” weekly and monthly, segmented by agent name.

Identify team members that are on their way to hit or surpass their goals.

Specifically, praise individuals that hit 70% of weekly goals by Wednesday, and those that surpass their weekly goals.

Personally speak with team members that fail to meet goals on consecutive weeks.

Specifically, look for lazy team members, and those that are holding less calls than others.

How do I set clear goals?

To ensure that there is clarity on expectations, I recommend adopting a SMART approach when setting goals. Being specific as to what we want to achieve helps to evaluate whether we’re making progress or actually achieved it.

What is the different between result vs. progress oriented goals?

Result oriented goals are achievements that one can hang on the wall: e.g. A series A investment into a company, a championship trophy, 5 years experience working at ______, etc.

Progress oriented goals are activities that we do while trying to achieve the result oriented goals: e.g. Improving the sales process at a company, training every morning to prepare for championships, taking a course to learn how to do a job or task better, etc.

In the context of setting goals, it is important to set both result oriented goals, as well as progress oriented goals. Whereas result oriented goals provide vision, progress oriented goals show team members a path to achieving the vision and feel successful along the way.

Assuming that a company’s end goal is to go IPO or hit $100M in annual revenue, it will likely take years to achieve its goal. So the journey needs to be paved with progress oriented goals that help team members feel advancement, see a path to success, and focus on learning relevant skills.

There are also many more opportunities to celebrate progress than there are opportunities to celebrate results, so teams that focus on progress are much more motivated. And when end goals are missed (which happens at the best of organizations), teams that focus on progress and have a growth mindset tend to reflect and make the necessary changes to try again, while teams that only focus on end results have a tendency to simply feel unsuccessful and beat down.

Other readings on goal setting I’ve found helpful:

How do I share constructive feedback?


As part of our job in helping people advance their professional development, we’ll come across situations where we wished an individual could have done better on XYZ. It may not always be easy to give such feedback, nor be accurately heard. Yet it’s our duty to actively give feedback, positive or negative. I’m therefore going to share a framework that can help achieve this without getting personal.

We explored in part one a communication framework to help assess whether a manager’s assumptions about a team member’s feelings are accurate. The same framework can be used to share feedback with an individual. Allow me to illustrate:

  1. First expose observations: As a starting point, we need to communicate specific actions, facts and events observed that led us to feel how we feel. These are non-negotiable and non-arguable elements. (e.g. I see that you’ve started participating and sharing your thoughts during brainstorming sessions on…)
  2. Next expose how you interpret these facts, your feelings: We will share how we interpreted these observations, and provide an opinion on whether the events were good or bad based on the context. (e.g. I’m seeing that as a sign that you’re really becoming comfortable sharing your thoughts and ideas with the team. Do you feel that way as well? )
  3. Give feedback on how to improve and grow: Finally, based on the events and interpretations shared, this is where we provide specific feedback to help an individual improve, call out something that we don’t want to see again, or call out something that we want to see more of. (e.g. I’m really happy that you’re putting the effort to frame your thoughts and sharing them with the team. I’d love for you to keep doing this. Please continue preparing your thoughts and allowing yourself to speak up at team meetings. Your ideas are very much appreciated.)

Special note on praising and giving positive feedback

happy face

Praising needs to start happening early in a person’s learning, especially when they get it right for the first time. It rewards good behavior, keeps them motivated, and guides an individual toward the ultimate target. When praising, it’s good practice to be specific in what a team member did well.

  • Specific praise: “Thank you for helping that client explore all potential options.”
  • Unspecific praise: “Good job with that client”

Relating back to results vs. progress goals, let’s also acknowledge that we need to praise both: Team members need to feel good about making progress and achieving results. If we only praise progress, it may undermine the need for team members to achieve results. And only praising results may lead to an unrewarding and even frustrating path to the end result, especially if it’s a long project, or if the end goals are still unclear.

Recommended reading:

Special note on reprimanding and giving negative feedback

 sad face

Reprimanding should only start after an individual has succeeded on a given expectation, and knows what “good” behavior looks like. It’s intended to reinforce good behavior once they’ve been able to achieve it.

Reprimanding before an individual has had a chance to succeed demotivates them and sets unreasonable expectations. How can we expect someone to get it right before they know how to get it right? It’s like expecting a person that has never skated in their life to win gold medal at the olympics for speed skating. Unreasonable. There is a process that we need to follow to properly guide team members toward success. We’ll explore how to coach and train individuals in part three of this handbook.

After a person has experienced success, a reprimand re-enforces the view that the goal continues to be important, that they have achieved it before, and that they can do better.

Similar to praising, reprimanding should also be specific:

  • Specific reprimand: “I saw that you dismissed a client’s idea before they had a chance to entirely communicate it. I’m disappointed that you failed to actively listen. You’re capable of achieving this as I’ve seen it before, so what happened?”
  • Unspecific reprimand: “I’m disappointed with what happened with that client.”

Recommended reading:

How do I make sure I’m heard?

be heard

While trust serves as a solid foundation to leadership, communication is our main tool. A leader that can’t effectively communicate their vision, their thoughts, or their decisions brings no value to the team: They don’t help set a destination, nor facilitate a solution to get there. As leaders, we must therefore learn to communicate effectively. Here are some outstanding resources on communication strategies to help us be heard:

Since most presentations today rely on digital slides or powerpoint, here are some good articles on how to avoid boring an audience:

If there’s one thing to recognize when giving a presentation, it’s that the audience can read much faster than the speaker can talk. With that in mind, I recommend to avoid putting into slides content that we plan to voice. Instead, slides should be used to complement what we have to say and emphasize a point: e.g. pictures, diagrams, or quotes that one wants to emphasize. This ensures that the audience is focused on what we have to say.

How do I make sure I’m understood?

Recommended reading: A case of misunderstandings

Saying something is not difficult. Saying it in a way that communicates the message accurately and that everyone understands is difficult. Too often, what we say is interpreted differently by different team members.

To be an effective communicator, we need to simplify and clarify.

Simplify the message

One method to simplify a message is to write it down and to strikethrough every element that doesn’t add value to the core takeaway. Any content that doesn’t directly help communicate the main message distracts the audience.

It’s a good idea to test one’s speech with a colleague to see if they remember the main takeaway that we intend to communicate. A simple message should be easily remembered and repeated by others.

Clarify the message

Beyond a simple message, a clear message ensures that the audience interprets the speaker’s words the way they are meant. This is accomplished by:

    1. Asking a member of the audience to repeat what we said;
    2. Providing relevant examples or analogies to illustrate the concept;
    3. Showing case studies to put things in context;
    4. Answering questions to clarify any confusions.

As best-practice, it is recommended to always communicate why: At the beginning of any message, simply describe why we’re here, why are we talking about this, why this is important, etc. This ensures that everyone is on the same page as to our goal.

How do I make the time to lead?

time agenda

To put the OMM management system (or any management system) into practice, we need to make the time to observe behavior, review work, prepare feedback, etc. More importantly, we need to recognize that this is part of our job, our time commitment.

Yet finding and dedicating time to managerial duties can be a challenge for all managers, especially new managers that may still be used to prioritizing individual work.

One solution is to schedule and block time for these tasks on the calendar, and respect it (this latter part is hard). Another tip is to be specific in describing managerial tasks to accomplish, helping to set clear scope to a task.

  • Specific task: Observe when a team member achieves _____ and praise.
  • Unspecific task: Observe team member behavior.

It’s important to realize that managerial work take more time to accomplish, so there is often no immediate reward. Individuals transitioning into leadership roles from non-managerial roles may find it particularly difficult to not feel instantaneous gratification everyday. To help with this change, a new manager can breakdown milestones into smaller tasks to feel constant progress. And to feel rewarded, I encourage everyone to celebrate every small accomplishment (e.g. give yourself a cookie every time you finish writing a chapter of the team’s quarterly report).

Recommended exercise

Let’s take some time to ask each team member: “Do you know what the success criteria are in your role?”

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