good things come to those who wait - actually - good things come to those who work like crazy and never give up

Becoming a Manager

As I’ve said before on this blog: when I started my career, it was never my intention to become a manager. I always wanted to be a software engineer (and one day an architect or principal engineer), and I worked really hard to deepened my technical knowledge  as I possibly could. I imagined myself working on increasingly important, innovative software for big companies or even overseeing my own software product one day, but I never saw myself as someone who would thrive in (or even be considered for) a management role.

Back then my view of managers included the pointy-haired people from Dilbert cartoons who seemed to do nothing all day long, but had irrelevant opinions on everything. I couldn’t see myself as one of those people at all. I hated meetings, I loved to get stuff done, and I was proud of my technical prowess.

But through a series of unusual events and opportunities, I rather surprisingly found myself in a leadership role not long after starting my career. It was the early 2000s, during the first dot-com boom, and during that time my boss made enough money during that time to quit his job and “call in rich”. Suddenly, there was no leader for our team and no one to represent us at meetings.

For a while I had pushed to have my say in what we built, not just how we built it.  And that desire to influence and impact decisions lead to more meetings, more email and presentations, and less writing code. My knack for breaking things down into simple pieces and my ability to explain the inner workings of technology to people less familiar with the system innards, lead to more responsibilities. Despite my surprise at landing in management, I found that I actually kind of liked it and could be good at it!
good things come to those who wait - actually - good things come to those who work like crazy and never give up


Becoming a manager early in my career was a surprise and a challenge. I was lucky enough to have a really supportive team that didn’t turn on me when I went from the their peer to their boss in a matter of half a year. But that doesn’t mean it wasn’t a bumpy road as I figured out this new role (for that time and for many years afterward).

One good thing about a big company, is that I received lots of training; people put a lot of energy and effort into helping me fit into my new role, and I put just as much energy and effort back into it. I attended classes, I read books, and I turned becoming a better manager into my personal passion and hobby outside of work.

Still, a lot of what turns a person into a successful manager is on-the-job training that doesn’t come from classes and books. While books taught me a lot of the skills and knowledge a good manager has to have, what I learned on the job had much more to do with my own personal development into a good manager and letting go of old mindsets and assumptions that prevented me from being as successful as I could be.

My biggest struggles included:

  • Learning to let go of praise and recognition
  • Taking blame for things that I wasn’t consulted about
  • Letting other people be the expert when I thought I knew more than they did


  • Allowing other people to make mistakes that I wouldn’t make or do things differently than I would
  • Mistakenly thinking that working hard could compensate for lack of experience (there are so many things that tenure, trials, and maturity teach you that just can’t be garnered from a book)


  • Being comfortable saying “I don’t know” (since, if you’re in charge, aren’t you supposed to know everything?)
  • Becoming the dreaded “one of them” in the office (in what I like to call the “us vs. them” mentality)
  • Investing in soft skills, business, marketing – and not deepening my technical expertise
  • Realizing becoming a better technologist would no longer be what made me better at my job.  And in fact being the best technologist on the team often means that you shouldn’t be the manager – you should be working in the technology.


  • Resisting the urge to jump and fix things myself (bugs, disagreements, specs, designs, etc.)
  • Giving other people opportunities even if I wanted them (going to conferences, new hardware or books, bonuses, gifts, dinners, or anything else where limited people can attend, or there are limited resources to distribute)

It’s humbling to see such a long list of things I struggled with, but there is actually a lot more I didn’t list!
For new managers, learning to think about your role in the company in a whole new way takes a lot of work to be really successful. You spend your entire career thinking one way (focusing on your hard work and individual achievements), then as a manager, you have to almost completely reverse it (ie. taking the blame when it’s not your fault, giving opportunities to others, etc.).

It’s not easy, but doing so is necessary if you want to succeed. You’ll be better at your job once you make the leap.

Going soft

As an engineer, I like data and systems. As a manager, I focus on people and customers (you could also say business). The most successful managers are the ones who are able to fully transition from being expert at the technical skills of their earlier roles to being expert at the softer skills required of leaders.

This is a hard thing for a lot of tech leaders to get used to, because nothing in our previous training prepares us for the emotional intelligence required in leadership positions. Being a good manager is all about empathy and communication, and there’s no formula or equation for that.

Letting go of programming

For a lot of former engineers, it can be hard to give up the job of creating code and building products. Changing your daily agenda to include meetings can be tricky when you’re used to working mostly independent all day.

I think it is incredibly difficult to be strong as a technologist and domain expert and be an amazing team manager at the same time (the only caveat being really small teams).  As I struggled to prioritize my new activities, and I had to resist the urge to squeeze in a bit of coding here and there.  An hour or two was barely enough to really dive into a meeting problem, and I could never reliably hit timelines with my largely interrupt driven schedule.  You just can’t be as good of a programmer as you used to be if you only have an hour a day to do it. Moreover, there is always more research, more learning, and more strategic work that you *should* be doing. As a result your focus needs to shift to your new responsibilities, and you have to give up control of your old ones.

This week our office was empty as many people were off and about enjoying their holiday vacations.  And when I went in the office I knew that I should be working on 2013 strategy, planning a team offsite, or laying out our team goals, but instead I spend my blissful day without meetings rewriting a portion of our iOS app.  It was so hard to stop even this weekend to write this post.  In many ways spending a few full days being creative and programming has been just too enjoyable to change back to my “management duties”.  However, I know that come Monday I will be back in the saddle.

Changing my focus

As an introvert, networking and relationship-building are not my favorite things to do, but as a manager I know that I am infinitely more successful when I have strong relationships with my team, my peers, and my higher-ups. It was a struggle for me to get used to the fact that its people and relationships that build success, not just output and execution.  I had to learn and make an effort to connect with people for the good of my work and the company, in spite of my inclination not to.

I also had to learn that other things besides technology matter for business. I once led a team at a startup where we completely discounted the importance of marketing, and though it was a surprise at the time, it’s no surprise to me now that that even though we had the best product in the market we were unable to capture the same market share as our competitors. As a leader, it’s your job to take into account all aspects of a business – not just what you happen to know.

Over the years, I have had many challenges. I’ve worked on teams where I have been significantly younger than the people I am managing, and others where engineers have been used to having no manager at all (and as a result downright resent authority and managers). Both of these were hard situations to walk into, and neither would have resulted in a  good outcome without patience, effort and relationship building.  If you hide in your office because you’re intimidated, overcompensate because you are insecure, or lash out because people don’t take you seriously, you’re setting yourself and your team on a path to failure.

And as a manager, a failing team means you are failing at your job. It’s not an employee’s job to do better for you; it’s your job to draw the best work from each person as possible.  And hopefully capitalizing on synergies that allows the whole to be even greater than the sum of the parts.

In both of the situations I mentioned, I was able to come out successfully because I prioritized the people on those teams. I got to know them, and made sure they got to know me too. I pulled out all my charm, all my empathy, and made those relationships my top priority.

Finding a balance

To me, being a successful manager is all about achieving balance (like so many things in life).

So much of the work a manager does is somewhat counterintuitive. Like when you see a problem on your team, it’s actually better to not jump in and fix it yourself; instead, you have to stay out of it and find other ways to guide the team toward a solution. Or when your team makes a huge miscalculation (one they might not have made if they had consulted you) and you have to take the blame (from your boss, executive team, or even the board of directors) even though you weren’t involved.

Sometimes it sucks. But being a good manager means always thinking in the best interests of your team and the company over your own personal interests or preferences. You’re trying to build the best team possible, and sometimes that means walking a fine line for what is best for the person, but also what is best for the whole team/company/organization.

For example, imagine sitting at your desk for a 1:1 with your very best developer. They tell you they are very interested in moving away from front end development and into data mining, or even becoming a manager themselves. In your head, all you want is for them to continue being the star of your team forever! For a company or organization, having a person keep continuing doing what their best it is often the best for the product. But that’s not realistic, and trying to force them to limit themselves and keep doing what they are doing will almost always blow up eventually.  Smart people like to learn and will seek growth opportunities, and if you don’t provide them then surely someone else will.

In these situations, I try to always do what is in the best interest of my teammate. I try to find a way to give people opportunities they desire, and connect them with people who can help them learn.   And I will be as transparent as possible to explain to corundum – because sometimes they can offer ideas or suggestions that help them grow in a specific direction, but can keep progress moving forward on their current responsibilities.

In almost all cases, if you do what’s right for the other person, you’re doing what’s right for the company. Give your star employee some freedom, and they may do their best work yet. Try to tie them down, and they’ll be out the door the second they get an offer from someone who will let them do their thing.

Being a leader

There are a lot of ways to go wrong as a manager (I’m sure many of you are nodding along with that statement!), and I am still not acclimated to many aspects of my role. I’ve been doing this for the last 7 years, and I am still always working on improving myself so I can be a better leader and teammate.

I swung back and forth early on in my career as a manager, trying to figure it all out. I went from terse and closed off (in an attempt to be more authoritative) to overly friendly and getting walked all over (in an attempt to be better liked). It takes time to find the right feeling for you and how you can be comfortable and effective.

At the end of the day, though, your job always boils down to keeping the company moving forward. It’s up to you to determine how best to do that. But if you ask me, being an incredible manager comes down to these basic principles:

  • Be a domain expert. I was promoted into management and have remained there because I am a domain expert. I learn every part of my company’s system, and I can speak intelligently about each of those parts. This is how executives do their job well.  You don’t have to be the only expert, but you better know your stuff.
  • Work with people. Being willing and proactive about communication is essential. What does your team need from you? What do your management peers need from you? What does your boss need from you? These are the questions that dominate your work.
  • Know how to ask for help. Just because you’re the boss doesn’t mean you should know everything. But it does mean you have to ask for help when you need it and not to wait until someone notices that you or your team are struggling. And in fact, letting other people be leaders, experts and authorities helps build a stronger team and better relationships.
  • Disseminate information up & down. As a manager, you are the link between your company’s leadership and your own team. This means you need to be aware of the goals and challenges facing the company, and calibrate your team’s projects and output to them. Likewise, it’s up to you to determine which of the successes and challenges of your team need to be addressed by the leaders of your organization.  Does your team understand when to hack something together or build a long-term robust solution?  Are you providing enough transparency up and down your organization?

If you can do those things and operate under the mindset of doing what is best for the company, you will learn how to put your own spin on everything so you can be authentic and successful in your role.

Lots of managers are concerned with developing their management style first, then getting the job done. I think if you can focus on the basic, driving principles behind what makes a great leader, then you’ll have an easier time being your authentic self. Being fake is how people get into trouble.

What if I don’t want to be a manager?

For most people, the path of promotion during their career leads them closer and closer to management positions. You might go from being a software developer to a team lead to a manager, for example, over the course of a few years of being really good at your job.

But for some people, ending up as a manager isn’t really their vision of personal success. Plenty of strong engineers and designers end up as managers and discover that all they really want to do is go back to doing their engineering and designing (sometimes I feel this way too!). Managing isn’t for everyone. It’s basically a whole new job description, and it’s one some people just prefer not to have.

Anne Kreamer – a former executive at Nickelodeon – wrote an awesome piece for HBR on just this topic. She is someone who, after being extremely successful in her previous roles at Nick, was promoted to an Executive Vice President role and started overseeing the people who were doing what she used to do: making cool programs for kids.  To her, missing out on the hands-on creativity of her former role made all the perks and new challenges of being an executive feel like it wasn’t a promotion at all.

This is an important lesson to consider for anyone taking on a management role. Are you suited (or interested in becoming suited) to this job, with all of it’s challenges and unique responsibilities? What would it mean to you to become less involved with the daily hands-on work of your company and more involved in the big picture development of it?

If you’re not interested in leaving your current position or becoming a manager, this post has some great ideas for how you can continue to increase your pay and importance to the company without giving up the work you’re really passionate about.

Want more information on becoming an amazing leader? I love this post from Steve Yegge, and here are a couple more good resources to get you started. I would love to hear what other managers have learned along the way and what challenges you’ve been able to improve from.

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