From Programming to Managing Managers: 5 Things I Learned the Hard Way

Leaders don’t become great because of their power, but because of their ability to empower others.

When I moved from being an individual contributor (IC) to a manager, my responsibilities shifted from doing work to getting things done through others. My job was no longer about the number of lines of code I wrote, what bugs I fixed, or the changes I pushed to production. It involved bringing people together, helping them realize their own potential, and empowering them to produce some of their best work.

The mindset shift from going solo to promoting teamwork, thinking about my growth to being responsible for others, and avoiding conflicts to embracing them took some time to get used to. I made plenty of mistakes, learned from them, experimented with new strategies, and repeated the process. The experience was rewarding and fulfilling. I was growing and learning — knowing there’s so much to do and finding ways to get better at it in some way was addictive.

My ability to approach change with curiosity and creatively solve big problems with calmness and strategy got me to the next chapter in my career. I was no longer managing ICs; I was now managing other managers. Being responsible for people who were responsible for so many others was nerve-wracking. The impact of my decisions and what I said or did was no longer limited to a few engineers. Even though I had a lot to learn, I decided to step up and be the leader my people expected me to be.

Here are a few practices that helped me become a better manager of managers. It includes lessons from some of the best leaders in the world and what I've learned through experimentation, trial, and error.

“Before you are a leader, success is all about growing yourself. When you become a leader, success is all about growing others.” — Jack Welch

Stay in Touch with Reality

Every step up the ladder takes you farther from people who do the real work. What you think you see and what you often hear may be less grounded in reality and far from the truth. The only way to bridge this gap is to stay connected to people in your organization who no longer directly report to you.

Keeping communication lines open with your indirect reports, which are managed by your managers, enables many things:

1. Gives you an opportunity to hear their real problems.
2. You can learn how employees feel about their managers. Knowing how your managers are doing enables more relevant feedback.
3. Gives them a channel to voice their concerns. They feel heard and supported by leaders in the organization.

A great way to stay connected and closer to reality is to do regular skip-level meetings. I scheduled a one-on-one with each of my indirect reports every two months. Making it a recurring meeting was the best way to remove the burden of decision-making and ensure it doesn’t get deprioritized. Find a frequency that works for you and your people – and stick to it.

“Leadership is solving problems. The day soldiers stop bringing you their problems is the day you have stopped leading them. They have either lost confidence that you can help or concluded you do not care. Either case is a failure of leadership.” — Colin Powell

Don’t Make Their Decisions for Them

It’s tempting to solve a problem. You’ve done it before as a manager, and you can do it again. However, the more you step in and take the lead, the less your managers will be equipped to deal with future situations.

A leader’s job in any organization isn’t to tell people what to do, be involved in every problem, or deliver 100% perfect outcomes. Their job is to grow their people — enable them to use their knowledge to make their own decisions, motivate them to build the skills necessary to feel confident, and use their own time effectively to look into the future and solve hard problems.

Be a coach, a great teacher. Give them the required context, but don’t make their decisions for them. Don’t dictate how a certain thing must be done. A great way to do this is to ask questions:

1. What challenges are you facing?
2. What solutions have you tried? What worked? What didn’t work?
3. What are other possible solutions?

“Whenever we work diligently, and possibly brilliantly, to advise others concerning decisions in which they are involved, their internal reaction may well be “This is great. She’s doing the work, coming up with all the ideas. I’m off the hook. And if her idea bombs, well, it wasn’t mine, so I’ll still look good. The bonus is, I’m not putting myself or my own ideas at risk. I get to stay safe.”

This conscious or unconscious internal response is incredibly expensive both for the organization and for the individual. Trying to build leaders by regularly exposing them to your brilliance guarantees a lack of development. You will not have allowed anyone around you to show up with solutions outside the reach of your own personal headlights. If your employees believe their job is to do what you tell them, you’re sunk.” — Susan Scott

Focus on Results, Not Likability

Want your managers to admire and respect you? Stop doing things that make you look good. Stop trying to please them. When your decisions are rooted in likability, you focus on being nice which prevents you from speaking your truth. You try to avoid disagreements, ignore conflicts, and hesitate to challenge them.

As a manager of managers, be kind, bold, humble, and thoughtful. You can care personally and challenge yourself directly at the same time. It’s your job to bring out the best in your managers and drive your organization toward excellence. You can’t do it unless you’re willing to make bold decisions and practice courage to stand out.

To bring out the best in your managers:

• Don’t sugarcoat feedback. They must learn to handle criticism even if it doesn’t make you look good at first.
• Hold them accountable. Teach them the value of making commitments and sticking to them.
• Instill hope for success and a belief in themselves. Encourage them to keep trying.
• Challenge them to step up and embrace opportunities to drive major initiatives, lead big projects, and do impactful work for their organization.
• Give them hard goals, not easy ones. Let them surprise you.

“Effective leadership is not about making speeches or being liked; leadership is defined by results not attributes.” — Peter Drucker

Listen, Challenge, Commit

What’s more important as a leader ― proving yourself right or making the right decision? I think the answer is obvious. Yet most leaders do the former — they let their egos get in the way. When proving your brilliance takes priority over making the right decision, you fail as a leader.

While having discussions with your managers, do this:

1. State your viewpoint, but also show curiosity to listen to them.
2. Ask questions to understand their point of view. Don’t reject anything without listening to it first.
3. If you disagree with them, don’t hesitate to state your opinion. Challenge them, seek clarifications, and dig deeper.
4. When it’s time to make a final decision, if the data stand in their favor, show your support and enable them to move forward instead of being stuck with your initial opinion.

“A strong leader has the humility to listen, the confidence to challenge, and the wisdom to know when to quit arguing and to get on board.” ― Kim Scott

Walk the Talk

The way you manage your managers greatly influences how they manage their own teams. Want them to give consistent feedback to their teams? Start giving consistent feedback to your managers. Want them to handle conflicts well? Start doing it yourself without ignoring or avoiding conflicts. Want them to speak up and disagree? Use every opportunity to engage in healthy disagreements.

As a manager of managers, what you do matters more than what you say. Your managers can’t take you seriously if you say one thing to them and follow a different practice yourself. It’s important that you walk the talk ― be consistent in what you ask for and how you display it in your own behavior. The best way to coach and teach your managers is not through speeches but by demonstrating it in action.

“People hear what we say, but see what we do…and seeing is believing. Words are just words…unless you live by them. You have to Walk The Talk.” ― Eric Harvey

Summary

1. Being a manager of managers is a great responsibility. Your behaviors and actions impact your managers and the people reporting to them.
2. As the gap between you and the employees increases, it’s hard to keep in touch with reality. Not knowing your employees' difficulties will prevent you from fulfilling your responsibilities. Reduce this gap by doing regular one-on-ones with your indirect reports.
3. Coach your managers and help them make better decisions, but don’t make their decisions for them. You can’t grow the people in your organization unless you also empower them.
4. Your managers will respect and admire you for your courage, compassion, and ability to make tough decisions. Don’t focus on getting them to like you. Worry more about impact.
5. Listen to your managers. Challenge their point of view. But don’t let your ego get in the way of making the right decision.
6. Don’t expect your managers to do what you can’t do yourself. Walk the talk. Your managers are learning through your actions.

This article was originally published in Better Programming.