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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