Growing Leaders to Solve the Hardest Problems

In an organization with many teams, problems will arise that span across these teams and require solutions broader than an individual manager’s purview. These types of projects include things like: introducing changes to a quarterly planning process, agreeing on broad architectural changes, rolling out a new project management tool, or making changes to how on-call is managed.

In a high functioning organization, leaders (often — though not exclusively — managers) will share the burden of solving these challenges. Through my years coaching managers and discussing with other engineering leaders, I’ve noticed that certain managers seem to take on more of this work than others. Diving deeper into it, there are a handful of reasons for this. Below is a summary of some ways we, as leaders, can help encourage others we work with to successfully develop solutions to complex organizational challenges.

How to Manage for this Skill

Consider each of these four areas for ways to remove detractors and increase motivators for those you work with:

Motivator (Gas Pedal)Detractor (Brake Pedal)
ExternalSupport and coaching, expectations to do this kind of work, recognition for this workTeam requiring lots of focused attention, organizational friction/complexity in the way, discouragement from other leaders, difficulty identifying a problem to solve
InternalDrive to improve systems, ambition, confidence in solution, skills in area, excitement to solve the problemAnxiety, low confidence in abilities

External Motivators

It’s best to begin by considering external factors, they’re more often in your control and more easily visible. A lot of these have to do with you as a leader, and possibly your peers or your manager’s behaviors. Does your organization reward and praise people for taking on this kind of hard work? If not, get started. (This is an opportunity for you to demonstrate some cross-team influence in getting other people on board to support your efforts here.)

It’s also worth being explicit with managers of your expectations for doing this kind of work and the value of taking on these types of projects. I would expect that every senior engineering manager is doing this type of work, and that nearly all engineering managers are starting to find ways to practice these skills, either through smaller-scoped projects or through helping others with their projects.

External Detractors

All of the right pieces can be in place for external motivators, but people may still require support clearing external blockers. Consider what friction, complexity, discouragement, or time demands are in the way of this person being successful? Can you remove them, or coach the person to remove them for themselves? Keep in mind, this may take dedicated effort over a long period of time. If, for example, the person has recently hired a number of new engineers, they may need to take 3 to 6 months to onboard those engineers and develop their team cohesion before they can begin to safely step away from being as heavily involved in the day-to-day.

However, you can still formulate a plan today, even if step 1 is: get your team into a good spot. Then step 2 is to revisit in 3 months.

In my experience, another frequent sticking point is in identifying a problem to solve.

If people are struggling with identifying problems they’re excited about solving, have them schedule meetings around the organization to ask others what’s currently frustrating them, what they’re worried about, or what problems they’re seeing. I use this strategy regularly and it never fails to produce a long list of improvement opportunities.

It can also work to give people problems to work on, but when they identify and articulate their own, it’s often much more motivating. That said, it can be helpful to review and refine the lists they produce, especially for newer managers who may have less organizational savvy or experience to inform their priorities. Do this gently though, as it can be demotivating to have all of one’s ideas shut down. Asking a lot of questions can be a good way to explore the value of their ideas without passing judgment. Having someone fix a lower-priority problem that they’re excited to solve is still a great investment in their learning and confidence, and is certainly preferable to doing nothing.

External barriers can also prove challenging for newer leaders in taking on cross-team projects. Learning to remove these external detractors is a large part of the skill set of solving cross-organizational problems. As you’re growing people to take on these sorts of challenges, letting them solve those that are within their skill level will help them develop and learn. However, if they are spinning their wheels for an extended period of time on the same problem, it can be helpful to aid them either by helping identify and implement a solution or by removing the impediment yourself if that is required. It’s preferable to help them learn to work through challenges themselves, but sometimes having a more senior manager involved can solve problems in minutes that may take them weeks or months. Getting blocked is demotivating, so you’ll have to make the cost vs. benefit call of getting involved.

Internal Motivators

For those with internal drive, it can be tempting to just stay out of their way, which is often an ok strategy. Even better is to engage with them and serve as a peer or mentor to help them solve the problems they have identified and are excited about. Likely you’ve made some mistakes and had the opportunity to learn from those mistakes. Perhaps you can help your report to avoid some potential pitfalls or roadblocks along their way.

Sharing their excitement and helping them be successful will ensure they keep finding new and more challenging problems to solve. Do what you can to make sure they feel supported and rewarded for the work they’re doing.

Internal Detractors

Leaders with internal detractors can be more challenging to address, as they are not always visible from the outside. Yet, as a leader or mentor, you have an opportunity to help others introspect to find opportunities to develop skills and confidence and to find problems that excite them.

If you continually observe someone avoiding opportunities for solving these sorts of challenges, do your best to identify where their gaps are: consider first if they have any external detractors: is their team requiring too much of their attention? Are they trying and hitting roadblocks? Assuming nothing obvious appears, it’s worth considering if perhaps they are missing the motivation, confidence, or skills to proceed.

Confidence often follows skills and success, so I will try to help people find projects that are just slightly outside their current set of skills — too far outside, and they will flounder and possibly fail, but inside their current skills they may not grow.

As they try and make progress on smaller projects, you also then have the opportunity to praise and reward them for those efforts and allow them to build their confidence through their successes.

It can also help to pair a newer leader with a more experienced one, to observe and learn on this type of cross-team project – therefore hopefully eliminating or reducing internal detractors. This can be a valuable stepping stone towards taking on ownership of their own problems and solutions.

Final Thoughts

These skills are a component of what makes great managers and leaders, but often take years to develop (and I would argue one never really finishes learning). It’s worth starting today to grow these skills, as well as removing structural roadblocks to success in your organization. But it’s also worth being patient, as it will take time to identify opportunities then coach and teach leaders through those opportunities. This process often feels more like gardening than building a bridge as it is rarely a simple, straight path, but rather one full of complexity and surprises (but that’s what keeps our jobs entertaining!). Like they say, the best time to plant a tree was yesterday, the next best time is today.

Thanks to Annie Shao, Will Mernagh, and Rachael Stedman for their invaluable consultation on this post!

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