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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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start⬆Mngr handbook pt. 1: What’s the first step great leaders take?

start⬆Mngr handbook pt. 1: What’s the first step great leaders take?

First, a personal story.

A new team member (let’s call him Carey) joined my start-up team from a PHD program, after becoming tired of the bureaucracy and slow pace of change in academia. It was Carey’s first job outside of research. He was super smart, learned the role quickly, and most importantly, offered a perspective and mindset unlike the rest of us. Instead of constantly seeking new way of tackling problems like many of us, Carey focused his efforts on recording knowledge, standardizing processes, and bringing much needed stability in our chaotic environment.

I really valued Carey’s contributions, so you can guess the disappointment when I received a resignation letter from him five month into the job. During those five months, I never received a complaint, never heard any negative feedback, and never got word that the work was uninteresting.

So what went wrong? I got some insight from the exit interview notes, in which Carey complained about almost everything related to his work: The long hours; the chaotic environment; the lack of documentation and knowledge sharing; the unreasonable customers; and above all, my failure as a manager to listen and help improve Carey’s life at the company.

The truth is that Carey didn’t trust me enough to share any of his feelings

The whole thing shocked me. Here I was, thinking that the individual was all happy, and learn from HR that the team member hated their work, and me. I could have easily categorized the situation as a cultural misfit, blaming it on the fact that Carey has never worked outside of academia, and that this job was simply too different. To further support such a hypothesis, Carey didn’t share any common interest with the rest of the team, nor was he in the same age group as them. If we were back in high school, Carey wouldn’t have been friends with most of us. But thinking along these lines would have been misleading and I would have missed the point.

The truth is that Carey didn’t trust me enough to share any of his feelings. The responsibility fell on me, as a leader, to create an environment where Carey and others are comfortable sharing their thoughts. I failed to do that. I had failed to establish a trusting relationship with him, and establish myself as a leader. As result, Carey joined another team.

So if there’s one place to start, let’s start by earning trust.

A manager is by default placed in a relationship with all those that they manage. As in any relationship, it cannot grow without trust. At start-ups, it is especially important for leaders to have the trust of their team members: The organization’s success has yet to be proven, and is probably a long way out, so a critical reason why team members are with the company is their trust in the leadership, and their ability to execute on a vision.

In part one this startup management handbook, we’ll explore concepts that will help a leader:

  • Build a trusting relationship with a team member;
  • Be heard effectively;
  • Connect with team members;
  • Communicate honestly with team members;
  • Make team members feel comfortable sharing feedback.

What are some great reads on trust building?

I’ve bought all the above books on Amazon for $0.01 used (+shipping), so money shouldn’t be a concern. Rather, the hard part is finding the time to really absorb the ideas they expose.  I guarantee that it’s time well-spent.  So beyond this point, I will assume that all readers have acknowledged the concepts explored in the above readings.

Do I understand my new team members?


Trust is built on understanding, so when we enter a new management role, it’s a good idea to first learn about the team.

As new leaders, we can spend a few weeks shadowing team members, taking them out for coffee/lunch, and scheduling recurring 1-on-1 chats. I personally take many walks around the office with team members. No matter how we choose to connect with the team, it’s important that we actively listen. Speaking from personal experience, talking too much and suggesting actions before understanding the full context of situations can diminish our influence, and in the worst case scenario, lose team members’  trust before even gaining it.

At start-ups, team members often expect direct access to their manager and senior leadership, along with opportunities to voice their opinion about anything related to the company or market. They expect to have a voice on how the company achieves its vision. I’ve personally witnessed many people leaving high paying jobs at established firms to join startups, looking to exercise more impact on their organizations. It’s thus critical that start-up leaders learn to listen to their team members effectively.

What should we observe in our interactions? Personally, I record every detail that will help individual team members feel fulfilled and help us achieve our team goals. I thus pay much attention to their:

  • Motivations that explain why the person does what they do / aim to do
  • Frustrations that get in the way of a person accomplishing their goal
  • Values that are critically important to an individual’s life, the disrespect of which will likely force them to quit.
  • Strengths which are areas, in the context of their role, where the individual currently needs relatively little help to accomplish.
  • Weaknesses which are areas, in the context of their role, where the individual currently needs external help to accomplish and improve on.
  • Perceptions that team members have of the manager, the team, and the company. I’ve found that perceptions can be more accurately assessed from a third party perspective, so I often try to review interactions from an external point of view or ask someone else to evaluate the situation.

It’s a good idea to record team member profiles based on the above traits, along with logs of conversations and performance reviews.  I keep a log of notes for each individual, separate from my work journal. This helps me reference past interactions, so that I am always aware of the context behind a team member’s thoughts and feelings.

Remember that people change, so a profile needs to be dynamic and updated with time. If a profile isn’t updated at least once a month, we failed to spend enough time connecting with the team member.

How do I hold a first conversation?


If we’re getting acquainted with new team members, or have just joined a new team, here are some questions that will help us learn about team members:

  • May I ask what a day here looks like?
  • What are your current priorities?
  • Which team members do you work closely with? And on what?
  • What do you really enjoy in your day-to-day and gets you excited?
  • What do you think this team does best?
  • Are you hitting any walls in your day-to-day?
  • If there was one thing that can make your life easier, what is it?

Note that most of our questions focus on facts rather than feelings. This is because it’s easier to understand why people feel a certain way based on facts.

Great team member engagement starts as soon as the initial interview

If these questions sound similar to interview questions, it’s because they are. A person’s growth path as part of a team starts from their job interview and continues on. So if we have the luxury of hiring a new team member, the interview is when we should start building a profile.

How do I stay in touch with team members?

Once we’ve had an initial conversation and drafted a first profile, we should never lose touch with a team member. This can be done via regular 1-on-1 meetings and informal check-ins. For example, we could plan for…

  • Weekly check-in to sync up on tactical items
  • Bi-weekly walk to chat and allow team members to vent and chat with us
  • Monthly check-in to discuss the team member’s professional development plan
  • Bi-annual reviews to formally assess the team member’s performance

The goal is to maintain active communication between the team member and us, their manager. I should make a note here that it’s helpful to have at least one meeting a month focused on just chatting about people’s feelings and perceptions on their work, and nothing tactical. This helps to gauge an individual’s overall happiness.

It’s also a good idea to give the responsibility of setting meeting agendas to team members. In my experience, letting team members drive conversations tend to reveal many unexpected thoughts that we’d never be able to seek out via our own questions. It forces them to think and prepare topics that are important to them, not just us. However, I still find it valuable to ask exploratory questions to help team members dive deeper into their thoughts.

How do I keep team members motivated?

Knowing what motivates an individual, what their career goals are, will help us align a team member’s ambitions to opportunities that the company has to offer. This helps put the right people on the right problems.

The goal is not to find a passion, but to help them look for one

Since not everyone shares the same goal, nor the same amount of clarity on their ambitions, we need to tailor the discovery process around individuals without forcing them to have answers on the spot. It can be very upsetting for a person to realize that there is a lack of professional goal in their life. An individual’s motivation is one of the most nuanced and challenging areas to explore.

For someone that does not have a clear motivation, I’ve often resorted to asking introspective questions about their interests and hobbies to kickstart the discovery process. It can take many conversations, many months, and even years for a person to discover a passion, so patience is key. The goal is not to find a passion, but to help them look for one – like many things in life, the journey is the important part. Some questions that can help us get started include:

  • What do you enjoy in your day to day work? Why?
  • What’s something new that you worked/learned in the past weeks, that you enjoyed or did not like?
  • What got you excited when coming to work this morning? Why?
  • I noticed that you really pushed yourself on XYZ, did you enjoy working on it?
  • I noticed that you’re reading about XYZ, is that something you want to explore?

For someone with a clearer motivation in mind, one can opt for a more conversational approach:

  • So your goal is to ___, do you already have a plan to make progress on it?
  • There’s an opportunity to ___ that may give you experience with ___, which is aligned with your goal to ___. Are you interested in pursuing that?

What if I lose touch with a team member?

At times, there can be misalignment between how a person is feeling, and how a manager wants them to be feeling (i.e. happy). It may be caused by situational changes at the organization, or changes in a person’s personal life. In those circumstances, it is important to assess whether the individual is feeling unfulfilled or frustrated in their job, in which case we need to allow them to voice it and potentially help improve things.

That said, it can be intimidating to address the situation. It will require a hard conversation to see whether a team member is frustrated, or if they intend to leave the organization. However, waiting to address the situation won’t help.

Proactively exposing assumptions and seeking validation will get a manager and the team member back onto the same page. To achieve this, I like to use a three step approach in assessing an individual’s actual feelings:

  1. First expose your observations: Communicate non-arguable facts and events that we observed (e.g. I see that you’re less participatory when it comes to brainstorming about a solution on ___ than in the past.)
  2. Then expose your feelings: Communicate how we interpret the observations (e.g. I’m interpreting that as a sign that you’re losing interest in ___.)
  3. Finally get on the same page with regard to the interpretation: This is where we simply ask “Am I right? Are there other things happenings that I’m not aware of?”

Assuming that the individual responds to our questions, it’s then our duty to shut up and actively listen. Success translates into a team member exposing whether our assumptions are right or wrong, and how they actually feel.

What is my role again?

Our job is to lead.

Much of what we discussed in this blog post focused on learning about team members, and giving them a voice. That’s not to be interpreted as “Let me find out what my team members want, so that I can give them everything they want.”

People are on the team to accomplish a mission, hit a team goal, and help the company move forward. So the insights that we learn from individuals need to be leveraged to help team members:

  • Successfully accomplish their work
  • Stay motivated
  • Learn & grow
  • Self-discover

Recommended exercise

Let’s ask ourselves “Do I know what motives each of my team members and why?”

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start⬆Mngr handbook intro: Lessons from leading my first startup team

start⬆Mngr handbook intro: Lessons from leading my first startup team

As a first-time people manager at a technology start-up (not a founder), I’ve made countless mistakes.

As result of my actions, people have quit, projects have failed, and efforts have gone to waste. My mistakes are the result of the trial and error approach I took in trying to get leadership right. Our start-up, like many other start-ups, simply did not have the resources available to get everyone proper leadership coaching.

For good and bad, we were left on our own to figure it out. I’ve thus learned the hard way that even with all the ambition, intelligence, and will power in the world, experience is irreplaceable in leadership, much more than any technical skills.

My hope is that by exposing my mistakes, it helps fellow start-up leaders get a head start, lead from insight rather than trial and error.

Why? Because ineffective leaders slow down others’ professional growth, end up frustrating people, and affect lives negatively. And I simply can’t stand watching well intentioned leaders not living up to their own expectations. Effective leaders will not only rapidly advance their own careers, but also help others achieve their full potential, push organizations to new heights, and make a positive impact in people’s lives. Yeah, it sounds rosy, but that’s how much of an idealist I am. Fact is, your success as a leader will translate into a better world for me as well.

What is a leader?

Before we get started, let’s get on the same page as to what a leader truly is. Google defines a “leader” as “the person who leads or commands a group, organization, or country.” I personally believe that our role can be more specific than that. I’ve always seen my role as three fold: To lead is to…

  • Set and support a vision that makes the world a better place;
  • Share and communicate our vision to gain support from others; and
  • Sustain momentum in the pursuit of our vision and always challenge the status quo.

Whenever I’m in doubt of what is the right thing to do, I remind myself of these core principles to get clarity.

Where do we start?

This 7 parts handbook is designed to help first-time managers gain exposure to core management concepts. Ideas exposed in this series helped me effectively grow a team of professionals from 2 to 20 individuals, at a start-up that grew from 15 to 120+ individuals in 3 years, successfully received multiple investment rounds from VCs, and also underwent a product pivot.

Here are quick links to the 7 parts of the handbook:

Welcome onboard and subscribe on the right!