Navigating the Leadership Labyrinth – A New Head of Engineering’s Journey

Sid Mustafa
May 28, 2024

Three months ago, Justin embarked on a pivotal journey as the new Head of Engineering at a startup, following the departure of the previous CTO. Commanding a team of eight, encompassing software developers and testers, Justin’s experience as a former team leader had primed him for this role. Yet, the path to leadership is often riddled with unexpected twists.

Justin rushed into “hands-on” leadership in a very independent and autonomous leadership group. He might need to pull back on that account and start from the position of trust – trusting his employees to do their job well.

Renata M.

Strategies Implemented

To forge a bond with his team, Justin introduced several initiatives:

  • Weekly one-on-one meetings to understand individual team members.
  • Discussions focusing on professional growth and career aspirations.
  • Active engagement in task execution for hands-on leadership.
  • Cultivating a friendly and approachable rapport.
  • Demonstrating best practices and exemplary work habits.
  • Assisting in problem-solving to foster a collaborative environment.

Challenges Encountered

Despite these well-intentioned efforts, Justin confronts a palpable barrier. The team views him as an outsider, their wariness manifesting in reluctance to engage fully. His approach, intended to nurture, is misinterpreted as micromanagement, leading to an atmosphere of confusion and demotivation.

The Key Question

How can Justin effectively bridge this gap and earn the trust of his team?

Your Thoughts

As fellow CTOs and engineering leaders, 

  • What advice would you offer to Justin at this critical juncture? 
  • Have you faced similar challenges in your leadership journey? 
  • How did you navigate them?

Let’s discuss strategies and share insights that can help Justin transform this challenge into an opportunity for growth and stronger team cohesion.

Share your experiences and tips in the comments. Let’s collaborate to create a roadmap for effective leadership in the dynamic environment of a startup. Your expertise could be the guiding light for Justin and many others in similar situations.

Peer Advice (Viable Solutions)

Renata M.

I think several things can be done starting with separating status report meetings from 1-1s and explaining the “why” behind weekly 1-1s.

It’s also possible Justin rushed into “hands-on” leadership in a very independent and autonomous leadership group. He might need to pull back on that account and start from the position of trust – trusting his employees to do their jobs well.

Understanding how things, people and the organization work should come before any changes.

Justin needs to focus on becoming the blocker removal personnel. He should be the force that helps get things done where needed.

This will help build mutual trust and rapport.
Once rapport is build he can lead his group according to his own vision, but taking into account that it might be significant change from what they had before.

Change takes time, even in a start-up.

Additional ideas:

Has Justin ever asked his employees what they expect from their leader and does he fit that image?

Is Justin applying the correct leadership style?

Maybe the collaborative and democratic style does not meet the current needs of the organization?

Paul C.

Simply said, people are uncomfortable with change. Going in guns blazing with these initiatives was a bad idea. The problems are relevant but the approach was wrong imo. This team is small, probably tight knit.

Perhaps Justin can organise a ritual reset/retro of the team, with a “I’m being a sponge” approach. Have the team describe what generally happens day to day, then address each of the 6 points as a “How might we”, if any of the rituals or points become a challenge/problem point.
Building rapport is equally as important as being a sponge, so asking the team for help in a meaningful sense to both Justin and team development, i.e. “I’m looking for an expert on this subject to help me with Y” rather than “I need you to do Z.”

Justin should prioritise the following day to day in everything he can do.
– Context (pulling it left and right)
– Communication (up and down)
– Consistency (of the above two)

Ken K.

Those are some great thoughts
@Renata M (and @Keith P) — I’ve found “managers”, even highly experienced ones, often don’t really know how to make 1:1s work effectively, and also struggle with how much (and what kind) of team interaction is best for their team(s).

With 1:1s are hopefully not the place for being “transactional”, that’s what status meetings or chats are for.

However, leaders in engineering tend to have a difficult time having effective regular meetings without that transactional “check off list”.

And for that matter team members often are of the same bent, and really want 1:1s to be transactional so it seems clearer to them.

To @Keith P’s point, weekly 1:1s that are simple calendar-ed 10-15 minutes chats are a great way to start down that road. Always go into the chat asking about the person’s life, make it personal, definitely steer it away from status updates unless something is just burning on their mind in that regard.

If anything more specific comes up in the short chats, you can schedule follow-on chats to discuss it, such as them saying “I really want to start working towards my AWS certification”.

Don’t problem-solve that immediately, but make definite time to dive into it more.

With Team Interactions (“active engagement in task execution”)
this one’s always tough as a Leader, because we want to help and are probably pretty darn good at the technical stuff.

It’s also extremely impactful if done right, building trust with your team, and having a “felt experience” of what they go through (with the “legacy code” and “tech debt” for instance), rather than just hearing second hand I’ve found being inquisitive, absolutely servant leadership oriented, and as Renata M
reminds – “Be the blocker remover”, not just at high-level, but even when looking at some code with your team.

Jamie C.

It’s a small team – make it fun. Be honest about the gaps in his own skills and that he is learning about the role – be humble.. Most of all, try and be that servant leader – if he can understand the things that make their lives hard and enable his team he will be successful.

Keith P.

I agree with Renata, it feels Justin might be jumping in with quite a procedural management style.
Building trust with less formal chats before diving in to growth and career aspirations, would be something I’d always do.
Asking the team where they might need help – more servant leadership

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  1. Mourad Z

    Before jumping on ceremonies with his team, Justin should instead focus on two primary areas:

    Understand the current state of affairs: what works well, what doesn’t, how is the current process working or not, the state of tech debt, where are the expertise and skills deficiencies, who are the leaders and those with potential and who needs help and coaching, etc. This takes time but through his interactions with the team, Justin would need to collect this kind of information.

    Understand where things should be down the line in terms of how he and his team can best support the business, deliver great customer value, improve the products, the operational efficiencies and others.

    Doing these two can occur in parallel and in the process, Justin can be transparent with his team about what he is after. That would open up his team, knowing that their new leader has a purpose in making things better. During these two activities, he should do a lot of listening while also articulating his objectives. These two combined nurture trust and inspiration. In addition, they would be the needed context for Justin to formulate, with help from his team, a roadmap to make things better. Priorities need to combine bottom up and top down feedback and he needs to be transparent about this. Where he sees conflict between these two, he also needs to be transparent and tell his team why their feedback is leading the way or why top down considerations need to dominate for the moment.

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