How good teams make their leaders better

Jolomi Otumara
7 min readJun 15, 2020

A lot is often said about great leaders inspiring their teams to take action, helping them navigate complex problems, steering them in the right direction and helping them achieve great success. Very little, however, is said about teams and how they make their leaders better.

When I say “leaders” here, I’m not referring to just high ranking executives responsible for leading large divisions within organisations. I’m referring to a leader in the most simplistic sense and by definition:

A person who leads or commands a group of people

Thus the principles below are just as applicable to the aforementioned executive as they are to a small-time manager, a government official, a parent, a business owner and their respective teams.

The calibre of the audience

To better understand how leaders might benefit from their teams, let us explore the effectiveness of audiences.

Digital ads targeted at educated classes typically take a different approach to those targeted at the semi-literate populace.

Similarly, separate software sales pitches to the technical and executive leadership teams of an organisation would likely take varying approaches; the latter focused on the high-level business details and justification for the software, and the former focused on the more intricate advantages and details of the day to day use of the software.

In essence, the calibre of the audience greatly determines the stakes and thus the approach and level of preparedness. Audiences enact a level of subconscious pressure on an individual that causes the individual to prepare accordingly. Let’s call this pressure, “audience pressure”.

Audience pressure is mostly a subconscious kind of healthy pressure and can greatly accelerate an individual’s growth. This is because the pressure itself leads to more thorough thinking, research, preparation and formulation of engagement strategies to get the best out of the time spent engaging with the audience.

Upward Pressure

Most individuals within and outside organisations work between 2 main audience groups. This isn’t any different for leaders. They are typically positioned between these 2 main audience groups; one above them, and the other, below.

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  • Upper management: Comprising of more senior stakeholders including a direct line manager.
  • Team: Typically comprised of direct reports.

Based on hierarchical constructs, pressure flows downwards thus individuals below invest more preparation effort to engage with upward audience groups.

Conscious and sometimes sub-conscious pressure heap flowing downwards

Good teams, however, ensure there is also upward flowing pressure to their leader. They do not simply take things at face value. They ask the hard questions and get to a place of alignment or compromise only because they find their meaning in what is asked of or communicated to them and deliberate to reach a shared conclusion. As a result, they force their leader to invest significant effort in preparation to engage with them. They make their leader think “if I took this to the team, they would tear it apart and possibly ask these 10 questions so I best be prepared with as many answers and detailed explanations to help them articulate the discussion”.

In essence, good teams do not shy away from mounting upward pressure on their leaders. They understand that upward pressure yields better preparation and better preparation comes from being more thoughtful, researching and exploring the “why” of various decisions, articulating the best way to explain and communicate decisions, devising the best way of presenting new information, showing a deep consideration for the team; all of which in turn helps their leader become better.

Good teams are deliberate about enacting upward healthy pressure on their leader

A blend of upward and downward pressure can place leaders in positions of greater perspective and strength thus driving them to become better all-round performers through the lenses of upper management and their teams.

Some guiding principles

Most individuals function in dual roles of leading teams and being part of teams led by other leaders, here are some guiding principles for both scenarios:

As a leader

You should aim to build up and empower your teams to become worthy audiences with the calibre that forces a level of preparedness from you that would, in turn, force your growth and improve your all-round quality. To do this, consider the following:

  1. Hire the right team: This isn’t always possible because in most cases, you simply inherit an existing team, but it is worth mentioning nonetheless. When you do have the rare opportunity of hiring members of your team, you should do well to hire individuals who have the calibre to mount some healthy pressure on you as the leader so that you can get better over time. You don’t want a “yes person” who would say yes to everything, challenge nothing, hold no opinions and simply do what they are asked to do without question — except you are in the military. You want individuals that can help you see things through different lenses, bring fresh ideas and perspectives to the table and challenge you positively.
  2. Create a conducive environment for healthy pressure: Some leaders struggle with this because they see alternative views and counter suggestions as a challenge to their authority. This should not be, and leaders should strive to create conducive environments for their teams to openly disagree, share alternative views, challenge one another with good intent and be vulnerable. This is what Amy Edmondson coined as “psychological safety” — a belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns or mistakes. Team members should trust that their inputs can be taken in good faith and not be seen as personal attacks.
  3. Ask your team the questions they ought to be asking: A familiar trope in most meetings is the sequence that goes like this; “any questions?” with *crickets* following and one person mustering just enough energy to say “no”. The role of a leader in these scenarios is to flip the table to ask the team questions they ought to be asking. Leaders can do this by mounting the pressure on the team and setting a precedent that if they do not ask questions, questions will be asked of them. In his book, “Death by meeting”, Patrick Lencioni highlights this as a role of a leader and goes a step further to say that a leader must mine for ideological conflict and drive that conflict to a conclusion.
  4. Be open to feedback: The openness of leaders to feedback is a strong signal to their team that their opinions matter. Leaders should not shy away from receiving feedback from their teams and more so, their handling of it, especially when negative, should be exemplary. In my experience, it is best to not respond to or defend negative feedback on the spot except if completely unavoidable. The goal is to let your team know that you have heard their feedback, you are grateful that they shared it with you and you would take some time to think about it and get back to them. Then make sure you get back to them.

As a team member

You want to mount the right kind of healthy pressure on your leader which would, in turn, improve their preparedness and the quality of your engagements with them. To do this, consider the following:

  1. Set expectations with your leader: Let your leader know the kind of person you are (or intend to be) if you plan to mount the occasional healthy pressure on them. Help them understand that your intention is not to stir up conflict, but instead to better understand their underlying thinking and to help explore alternative ideas and approaches where available, to ultimately yield the best outcomes.
  2. Care personally, challenge directly: The word “challenge” has a competitive connotation so it is no surprise that leaders occasionally get into a competitive mindset when they are challenged by their peers and even worse by their direct reports. Kim Scott coined the phrase “radical candor” as the combination of caring personally and challenging directly and even though there is a greater emphasis on “manager to direct report” relationships, I have found this to be just as effective in the reverse. You should care about your leaders perspective, stance and invested efforts on a subject and that should be clear in the way you communicate before challenging it directly or proposing an alternative.

The improvement loop

A core attribute of great leadership is the ability to bring out the best in those we lead. Those being led, however, also need to be deliberate about bringing out the best in their leaders. And even though scenarios, personalities and context may vary, being a conduit of healthy pressure goes a long way to making leaders better. A better leader is more than likely to make a team better thus creating an improvement loop.

The improvement loop: The team makes the leader better and the leader makes the team better

We all get to function in leadership and team positions in various capacities and stages of our lives so we should look to build improvement loops in our teams to make each other better.

A generation of future leaders is needed to advance the African continent and the world at large and with some luck, these improvement loops can speed up the process of creating better leaders.

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Jolomi Otumara

Product Leader & Venture Builder. CEO/Co-founder @ Partcloud, Prev Director @ Andela. VP @ SlimTrader.