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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?”

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!

Top 3 books for start-up managers

Top 3 books for start-up managers

One of my favorite books of all time is “Predictably Irrational” by Dan Ariely.

While not truly a management book, it completely changed the way that I interact, help, and work with people. It was an eye opener on the way that we behave as human beings. I read it when I was in first year of college. Back then, I used to read about a book or two a month. I loved being inspired by ideas from people with more experience and knowledge than myself.

After joining a startup, I rarely read. In fact, I piled up so many books “to read” that I’ve had to buy two new bookcases. The reality of start-up life meant that I was constantly reacting to the present, and spending the rest of the time planning for the future. I thus rarely had time to reflect and look into the past, learn from others’ mistakes and insights. By not reading, I knew I was doing both my team and myself a disfavor.

So I forced myself back into reading. I dedicated time in the morning and on weekends to read. My goal was to at least read one book a month. I averaged three. The result? In the first month after I restarted reading, I had more ideas than the entire previous quarter. I also became more self-aware, recognizing many mistakes and weaknesses that were limiting my leadership. Most importantly, I felt reinvigorated by all the new ideas and thoughts I was exposed to. I became more confident of my team and our future.

Of all the books I’ve read to date, the top three that had the most profound impact on my leadership, and in turn the professional life of my team members, are:

  1. The One Minute Manager: A concise, short read, that reveals the essence of people management.
  2. Competitive Strategy: The bible on strategic planning. Most start-ups make the mistake of doing everything for everyone in their early days – this book shows you how to be more strategic and choose what not to do.
  3. Are Your Lights On?: The best book on problem solving I’ve come across. Why? Because it’s not about solving problems, but rather defining them. We waste so much time solving the wrong problems – this book will save you that time.

Comprehensive list

That said, I obviously can’t just stop at three, so I’ve also shared below a collection of books I’ve recommended to fellow friends and colleagues.

start⬆Mngr handbook outro: Advance your leadership career via feedback

start⬆Mngr handbook outro: Advance your leadership career via feedback

We started this handbook with a discussion on how to gain trust. In this outro, I’ll discuss how to maintain trust. After all, what’s the point of gaining trust if we can’t keep it?

At start-ups, team members are typically young, intelligent, ambitious, and outspoken. They have an opinion on everything. Therefore, trust from team members is often built on a leader’s ability to seek and acknowledge people’s feedback. And the more trust you get from team members, the more they will do for you.

Yet with authority, it becomes difficult to gain feedback. People generally do not expect to tell their bosses how to do their job, and may even expect that they do their jobs perfectly. Team members may also dislike sharing feedback with their boss, fearing that it creates disagreements: A conflict where the boss most likely wins.

It is thus critical that we create an environment where team members are comfortable sharing feedback. Here are some tactics to help get started:

  • Set a clear expectation of what you want: This can be achieved by regularly prompting for feedback in different ways and praising team members when they act on it.
  • Establish a feedback channels: We can create processes by which team members can give feedback. Perhaps an anonymous survey goes out once a month, or every other one-on-one meeting is dedicated to team members sharing feedback. Simply saying “I’d love to hear your feedback anytime” is never enough. Team members still won’t know how to communicate their thoughts and feelings. Establishing feedback channels and holding team members accountable can facilitate this process.
  • Empathize: It’s important to put ourself in a team member’s shoes before taking a decision or announcing a change. This allows us to foresee how team members will react, allowing us to tailor our communication and roll-out strategy accordingly.
  • Eat the same food as team members: To effectively empathize, it helps to eat the same food, or do the same work, as front-line soldiers, at least once in a while or continuously in small doses. This also communicates to team members that you have the context to understand their pains.
  • Listen: Being an active listener will help team members feel that we understand them and acknowledge their concerns.
  • Respond to feedback: Acting on feedback translates into caring for the team. In the case where we disagree with a feedback, it’s important to clearly explain why that is the case and invite a constructive conversation. This ensures that team members understand our reasoning, even if they disagree with it.
  • Distinguish venting from feedback: There are times when team members want to vent and complain about a situation. It’s important to distinguish when that’s the case, versus when they’re providing feedback. Getting clarity ahead of a conversation ensures that we do not try to solve a problem when all that’s asked is a pair of ears to listen; when a person vents, they simply seek someone to listen, not necessarily respond. It is reasonable to simply ask the team member whether they want to vent at the beginning or a chat.

Recommended exercise

Lets ask team members for constructive feedback in a safe environment (e.g. Submit anonymously written notes)

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start⬆Mngr handbook pt. 7: How do I make my boss happy?

start⬆Mngr handbook pt. 7: How do I make my boss happy?

First, a personal story.

After spending two years as a decent individual contributor, I was promoted to team lead. It would be the first time that I manage people. How exciting!

In my first few weeks as manager, I didn’t really do anything different, aside from having one-on-one talks with my new direct reports. I didn’t change how I interacted with my boss, and continued to hold bi-weekly meetings to report on my priorities. I let operations run as normal and only intervened when team members needed my help.

Everything seemed great at first, but after a few months, I started to feel like I wasn’t doing enough, and wasn’t growing as a leader. I had a rough sense of how my team was supposed to help advance the company, but I didn’t know if our innovation initiatives were aligned with that of other teams. Yet I didn’t want to bother my boss with my problems; I didn’t want to reveal that I felt insecure in my new position.

Every week that passed felt worse and worse. I started to feel incompetent as a manager, unsure of where I was supposed to lead my team. My boss rarely provided feedback, so I didn’t know whether my team and I were successful.

One day, I finally rallied up the courage to tell my manager: “I don’t know if I’m successful or not. I don’t exactly know what results are expected of my team. We work on a ton of projects, but I don’t know how they relate to the overall company mission. I also don’t know if I’m acting as a good leader and would like some mentorship and coaching.”

What ensued was one of the most productive conversations I’ve ever had. Turns out, my manager made the assumption that I knew how our team’s priorities related to other company initiatives, so it was never discussed with me. We took the time to clarify all of that. On the management coaching side, my boss also didn’t know I needed it as I was doing fine. We then setup a mentorship plan, and also involved another manager at the company so that I could get two perspectives instead of just one. That night, I felt relieved and re-motivated. I found clarity on what was expected of me. I was confident that my team was advancing toward the right direction, and I personally had access to two mentors to guide me.

What did I learn? That not having clarity on what my boss expects of me leads to a stressful, confusing, and unpleasant time. The more time I let pass without clarifying expectations with my boss, the more insecure I became.

Since my manager interacts with many people daily, they may assume that I know things that are actually news to me. It is thus my job to communicate what isn’t clear to me.

In part seven, I’ll discuss how to manage up and stay in sync with our boss. This will help:

  • Understand what our boss expects of us;
  • Meet our boss’s expectations; and
  • Hold tough conversations with our boss.

Recommended Reading

What does my boss expect of me?

As our responsibilities evolve, our manager’s expectation of us also evolves.

Whereas a nurse is expected to report on his/her patient’s status and health, a nurse leader is expected to report on his/her team’s performance.

As we work to understand what is expected of us, it’s a good idea to share with our manager the management system we use (if they are not already aware). This ensures that our boss knows how to communicate  expectations with us, and more importantly, how we want to be held accountable.

Once a management system has been agreed upon, we can ask for clarity on their expectations of us: What goals they want us to achieve, what weaknesses they want us to improve upon, and how they envision us growing professionally.

We can also take it a step further and request direction, support, or coaching in specific areas to help our manager understand where and how they can help. This saves them time in diagnosing how to spend their energy with us, in addition to showcasing our sense of self-awareness. And fact is, most managers won’t find the time to diagnose where we need coaching, so let’s facilitate their job and ask for it.

Here are some questions that can help us clarify expectations of us with our boss:

  • What are the performance indicators or success criteria that will be used to assess my role and responsibilities?
  • What is the preferred method to communicate updates on my progress? 
  • What is the preferred method to communication update on my team’s performance? 
  • What is the preferred method for me to give and receive feedback? 

Who is my boss?

It’s also critical to understand our manager, the person. Insight on the person provides the necessary context to explain why our boss expects certain things from us, and behaves the way they behave.

It’s thus a good idea to observe and record our perception of our boss’s motivations, frustrations, values, strengths, weaknesses, work styles, and perceptions of us, in the same way that we keep dynamic profiles of our direct reports. In addition to understanding the boss’s frame of mind, this also helps us tailor our priorities accordingly. For what’s important to our boss should also be important for us.

How do I give feedback to my boss?


It’s not natural for most individuals to give feedback to their manager. We have a tendency to expect our leaders to know more than us, to be self-aware, and to not need our feedback. We may even expect our boss to be perfect. Yet nothing could be further than the truth.

Nobody is perfect (even definition of perfect varies from person to person). Nobody knows everything. Nobody can assess their performance objectively. Nobody can be certain of how they are perceived by others.

It is thus critical to proactively give feedback to our boss, to ensure that they know how to work with us effectively, and help us achieve our full potential.

Here are some tips that can help us give feedback to our manager:

  • Develop trust: Without trust in us, a manager is rarely going to listen to anything we say. It’s thus critical to show that we understand the problems faced by the team, along with our boss’s priorities. Once trust has been established, we can begin to share feedback.
  • Agree on a feedback system: Proactively asking the manager how they’d like to receive feedback helps establish a channel where feedback can flow.
  • Be transparent with our intentions: If we are planning to communicate feedback, we should let the boss know in the beginning of a conversation.  e.g. “Would you mind if I shard a point of feedback with relation to the situation around ______? I’d love your thoughts on my interpretation of the situation.”
  • Be specific and provide evidence: To avoid any opportunity for debate about the feedback, we can take the following approach:
    1. Find and communicate non-negotiable evidence that support our thoughts and feelings around a feedback. e.g. “Earlier in the ___ meeting, you dismissed Taylor’s opinion.”
    2. Share interpretation of the observations and communicate how their behavior impacted us, the team or the company. e.g. “The quick dismissal of Taylor’s opinion makes it uncomfortable for the rest of the team to share their thoughts openly.”
    3. Share a potential solution, while giving them the benefit of the doubt that they meant no harm. e.g. ” I know that you didn’t mean to hurt Taylor or shut down her idea. There was probably a distraction in the moment. To help keep conversations constructive in the future, perhaps you could share with Taylor how she can share opinions the next time? Or perhaps educate all of us on how we can constructively share feedback?
  • End with a praise and vote of support: A vote of support to our manager helps them understand that we are trying to help improve a behavior, and not attacking them personally. e.g. “I care about this team and this company, and enjoy our relationship. I thus want to make sure that the entire team feels this way and have the same supportive and constructive relationship we have.”

It’s important to realize that managers and leaders seldom receive feedback from direct reports. More often than not, direct reports simply get frustrated and leave the organization before trying to communicate feedback. That’s a shame. To help us avoid this fate with our boss, I highly recommend the adoption of a clear feedback channel between both parties. Give your boss a chance.

Recommended reading:

Recommended exercise

Let’s pick a frustration or issue that we have with our boss and work to communicate it to him or her.

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