5 things I learned the hard way as a manager of managers

When you go from being a manager of individual contributors to being a manager of managers, you are again going “once forth unto the breach” and pushing yourself out of your comfort zone. You’ll learn from new experiences, from your successes and your failures. Here’s some things that I learned, sometimes the hard way, that might make your transition to a manager of managers a little easier and more successful. Good luck and God Speed ⭐️️️️️️

1) Adopt a good book

There are so many books written on the topic of growing as a manager, however my favorite one is The Leadership Pipeline. Why? Because it not only explains what you do at each level of the management food chain, it explains what you don’t do. It also explains how to diagnose if you (or those around you) are not doing so well and what to do about it.

Over the years I’ve found this book not only as a useful guide for my own behaviors and growth, but also to create a neutral, shared mental model to use with my peers and with managers who work with/work for me.

I’ve found that the book has sometimes had gravitas and authority when I have struggled for it. It’s been a great coaching/teaching aid. And becoming great at coaching and teaching is essential as we’ll see in the next section.

2) Learn to give great feedback and be Radically Candid

One could argue that this section could also be titled as “read another couple of great books”. There are two books in people management that are bibles for me when it comes to giving feedback. The first is Crucial Conversations, the second is Radical Candor.

Crucial Conversations: I’ve attended classroom training on this topic twice. I’ve read the book about 3 times. I’ve downloaded the executive summary to re-read before having a high stakes conversation with someone or to pass it along to someone else who is about to have to have a tough conversation, about 100 times. There is no better book. It’s the gift that keeps on giving. Why? Because as you go up the management chain, having high stakes conversations is what you do. If you can’t master your emotions, practice masterful empathy, gain clarity of thought and deliver great feedback then you’ll never reach your full potential and, at this level, you’ll be letting down the people who rely on you for their own growth.

Some of my favorite highlights from this book is the “Start with the Heart” section. It teaches before you go to give feedback to anyone, start by working through the following inner dialogue:

• What do I really want for myself?
• What do I really want for others?
• What do I really want for the relationship?
• How would I behave if I really wanted these results?

These are simple but hugely impactful questions. By writing them out in bullet points I’ve often changed my perspective, cooled down and been able to move forward on a much better course than before.

Next is the STATE framework for having the actual feedback conversation:

• Share your facts. Start with the least controversial, most persuasive elements from your Path to Action.
• Tell your story. Explain what you’re beginning to conclude.
• Ask for others’ paths. Encourage others to share both their facts and their stories.
• Talk tentatively. State your story as a story — don’t disguise it as a fact.
• Encourage testing. Make it safe for others to express differing or even opposing views.

Following this framework to map out a feedback conversation (or email) has been immensely useful and made it easier for me to do the right thing by the person sitting opposite me.

Radical Candor is something that can take you to another level of openness, awareness and effectiveness. It teaches you how important it is to develop real authentic relationships, with openness, vulnerability and trust, with your team.

This book challenges and enables you to be more open, more humble, more vulnerable with those your work with. Done right, this can help you develop a higher level of emotional intelligence, which in turn enables you to move faster and better as a leader, with less collateral damage.

3) Learn to be a great teacher and coach

One of the reasons you got to be a manager of managers is probably because you are a great frontline manager yourself. However, now that you’re a manager of managers, one of your most important duties is to select/train/up-skill other great managers. Why is this an important thing to call out? Because it’s quite possible that you don’t yet fully understand or realize all the things you do that make YOU a great frontline manager. There are likely, good, valuable things that you do instinctively that you don’t realize. You’ll likely really struggle to identify all of these things up front, let alone figure out how to teach them to the folks on your team.

Another reason is that as a manager of IC, you can sometimes get away with a slightly more directive style at times, but you likely won’t get away with this style managing managers — you’ll wind up being called the dirtiest of words — a “micromanager”.

So what do you do about these two things?

For one, you can do some self-reflection, reading and soliciting for feedback and advice to help you understand and systematize your own management style and philosophy. Probably one of the best ways to do this is asking your boss, your HR BP, a trusted peer and maybe one or two skilled, trusted engineers who’ve worked with you for a while the following … “what is it about my leadership and management style that you think works well for me and why?”, “what do you think I do well that I should be trying to pass along to managers who report to me?”. The people close to you are the ones who can help you uncover your strengths and blindspots best, be open and brave to ask for their help. Couple this advice and feedback with self-learning from books and course and then write down what you want to teach/pass on and get some final feedback and advice from your boss or a peer before going gungho to teach this all to your new manager reports.

All of the above might sound slow and laborious, but you only make this transition once, it will stand you in good stead to go a little slower right at the start to go faster in the long term. I think you can get all of the above done in about one or two weeks of elapsed time, so that’s not too slow 🚀

Now that you’re all set on what to teach, my advice is to learn how to coach, rather than tell. Learn how to weave in a socratic method of teaching. One of my favorite books is The Coaching Habit, because it’s got great content, advice, stories and is available as an audiobook as well as paperback and kindle (I’m a huge fan of audiobooks as a medium for learning). IMHO coaching is an important and empowering management skill that you have to develop to be a successful manager of managers. You’ll fail without it.

4) Learn how to stay connected to the people, teams and projects in your org

As a manager of managers your day is stuffed full of management meetings of some form or other. Be it strategy sessions, recruiting syncs, headcount planning foo, comp reviews or 1:1’s with your direct reports. You’ll likely have very little free time for anything.

How do you make time to stay connected to the people in your org who don’t report to you? To the projects going on in your org? To team health? How do you not become an abstract, ivory tower egghead who everyone thinks is out of touch with reality?

If you don’t find a way solve these things, you will lose the trust and credibility of your org (and your boss). When this happens good people will start to leave your org and you will start to make bad decisions on behalf of your org. Then you’ll feel bad and either quit or be moved out of your role.

So, this is important, what should you do?

The honest answer is “I’m not sure”. There is no one size fits all here, no silver bullet, different things work for different org sizes and you need to keep evolving.

Some things that have worked well for me (my org has 6 teams with 42 people in total) include:

• having a 1:1 with every new person that joins about 6 week after they start to mutually introduce ourselves and start to build a human relationship so that hopefully if they ever need to ask me something or we need to give each other the benefit of the doubt on something, that this will be possible.
• have small-group skip level 1:1 where you meet with random groups of people and ask them how things are going
• make sure you always know what the hardest problem/project on each team is. Schedule time to talk with the team directly to have them explain to you what they understand the business problem/opportunity to be and how they intend to solve it.
• be as open, vulnerable, transparent and radically candid as possible in any group meeting / all-hands as possible.
• send out status emails to your group explain what your goals are, what you’re doing and again be as pen, vulnerable, transparent and radically candid as possible. Model the behavior you’d like to see from others.
• use anonymous surveys (like the google re:work one or culture amp) to get feedback on how you’re doing and how else you might improve in this area

5. Set Goals for yourself

You probably thought you had little time to do “real work” when you were a manager. Well my experience has been that you’ll likely have even less “slack” as a manager of managers. You’ll start getting escalations from your teams, you’ll be involved in more cross-functional work, regularly occurring “run the business” meetings will start dominating your calendar. If you don’t set deliberate strategic and personal development goals for yourself you’ll easily got lost in a sea of reactive work. If you do this, you’ll stagnate and be mediocre.

My tips are to manage your calendar proactively. Pre-schedule bigish blocks of contiguous “focus time” each week where you can get your own thinking or work done.

Document your own annual, quarterly and weekly goals. Share them with your boss and team to build accountability to find ways to prioritize them and make them happen.

Ultimately your legacy in a role is not about the things you reacted to, it’s going to be about the change you drove. This won’t happen without deliberate focus.

Closing thoughts

I’m doing a lot of writing these days, because it helps me get clarity of thought to work and teach better. If you like my thoughts or like the company culture they portray, then DM me, I’d love to chat, we’re always hiring for kind, thoughtful leaders in Dublin, London and San Francisco ⭐⭐⭐️️️

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