Obi-Wan Kimberly Is Your Only Hope

“who’s able here to honestly say ‘I have a great boss’?” two hands raised… 320 persons in the room… Via Daniel Glazman on Twitter

Although I always identify myself as a technologist, I’ve been managing people for a while and that is the primary focus of my full-time work. Managing people is an art, not a science. It’s very hard work, and I didn’t completely understand this before becoming a manager. Honestly, I don’t think most people — even managers — understand how hard of a job this can be.

I think that I’ve become a pretty good manager — with time and experience, with feedback and mentoring. There were times when I wasn’t so great, though. In an attempt at radical honesty (hat tip to Erica O’Grady), here is a list of my epic management fails and what I’ve learned from them.

• I tried to keep my hands in the code. Somewhere I once heard that coders who become managers and still try to write code only do so because they’re arrogant and they end up sucking at both. While I don’t agree 100% with that statement, I can agree that diverting focus from management responsibilities can have a negative impact on people and projects. As a manager I’ve gotten so deep into code that I’ve trampled on the responsibilities and goals of my direct reports. I’ve also made commitments to deliver production-ready code but then been so distracted by management responsibilities that I caused project deadlines to be missed. While attempting to code for production work isn’t a good idea for managers, I think that coding for practice — to keep one’s skills in shape or to have experience with what the team is working on — is definitely a good thing. A technical manager who can coach a team on both a personal and a technical level is a huge asset.

• I didn’t prepare for one-on-one meetings. One of the top priorities of a manager is meeting with direct reports on a regular basis to review expectations, set and track progress of goals, provide feedback, and coach for achievement. If you ignore this responsibility as a manager, you’re not doing your job, period.* Over time, I’ve realized that some managers avoid these meetings because they’re not prepared. I’ve certainly made the mistake of meeting with an individual without having an agenda, or without having deliverables ready. Ever had an awkward review with your boss? Chances are, it was awkward because they weren’t prepared. I find that I have to practice difficult conversations before I walk in to a meeting, and I even like to rehearse giving feedback. When I’m nervous about a meeting, I know I’m not prepared. When I realize this, I’ll try to reschedule the meeting or, worst case scenario, I’ll admit to being unprepared and beg forgiveness.

  However, even if you conduct regular one-on-ones, you can do it very poorly. For example, I’ve had managers who’ve spent most of my one-on-one time talking to or emailing other people, just talking the entire time without listening, and even zoning out (staring at the ceiling, a piece of furniture). Other faux-pas include glaring at the person (or eye-rolling, laughing at inappropriate times), only giving negative feedback, never offering assistance, and never asking for feedback.

• I wanted more (or less or something different) for someone. I’m an overachiever and I’ve always had a vision for what I could and should be doing in any job. I know that not everyone is this way, yet somehow this fact escaped me early in my management career. Some of my earliest supervisees were just doing a job, with no vision for themselves in the future, so I adopted a style of pushing my own vision for a person’s career. I could pat myself on the back for the times in which this worked out, but there were times where this approach certainly backfired — such as the strong generalist who I thought should specialize in an area they didn’t care for, or the developer who I saw moving up the tech ladder when they wanted to move into management. Having a dialog not just about about an individual’s current role and goals but also about their future is crucial. I like to do this at least twice a year, now, to ensure that my direct reports and I are on the same page.
• I hired someone despite having concerns about their ability to do the job. This is a tough one to address in generalities, but I’ll try. Any hiring decision should be backed up with evidence gathered through a rigorous interview process. Every new hire presents some level of risk, but you want to have primarily positive feelings about a hiring decision, not concerns. I have, on occasion, made hiring decisions based less on evidence and more on what I thought could be possible, given training, coaching, and mentoring. Sometimes it has worked out wonderfully. Other times it’s been a painful experience for both the individual who was hired and for me. I do believe in giving people a chance, though, so I can’t totally knock taking these risks. These days I try to be open about expectations prior to hiring and I reinforce those expectations once the individual walks in the door in regular one-on-ones. I don’t usually out-and-out express my concerns, though — this can kill a person’s confidence! But if I must, I’ll also express my support for the person and assume responsibility for making sure the right things are in place for the person to be successful.
• I let my own issues get in the way of my responsibilities. Anyone who’s followed me on Twitter for the past year has seen this one first hand. I started a new job last January and spent almost the entire year unhappy with my role, the work, and number of other things. I focused on the frustration, vented publicly, and let public response further fuel my discontent. All of this distraction consumed me; meanwhile my team languished. I began planning an exit strategy and engaged an awesome career coach who ended up reminding me of my strengths and reignited my passion for creating positive change. I set to work on creating a plan to address not only what was making me unhappy but also what I felt was missing from making our organization a powerhouse. I’m now executing on that plan and seeing small successes, which I hope to grow into larger successes this year.

Do you recognize any of these epic fails, either personally or in a manager you’ve worked with? Does your organization have a strong culture of coaching and mentoring managers to prevent against these and other fails? Share your story below for others to learn from. I’ll share my epic wins later!