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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