Becoming a better manager

By @ryantmcknight | Posted: March 05, 2017

NOTE: This post captures my evolution as a manager from Nov. 2014 – March 2017.

More sleep. A real vacation. Less stress. That’s what management meant to me in November 2014.

When I first became a manager, it was out of necessity. I needed help. At the time, I was the only designer at Industry Dive, a B2B media rocket ship, and the projects were hitting my inbox faster than I could read the requests. So I made my first hire, and my quality of life improved.

Then I started to grow. The transactional perspective with which I began slowly shifted to one focused more on individual and team development.

Somewhere along the line, I realized that effectively delegating tasks and knocking out lots of “wins” for the company did not make me a better manager.

What made me feel like a better manager were hard-earned habits like being the last to speak in my team’s meetings, aligning my team members’ interests with their project assignments, and leaving my personal problems at the office door.

Adhering to approaches like these demands a significant amount of mental effort and attention. There are no shortcuts.

Below are a few questions I use to routinely self-assess and reflect on ways I can improve.

Q. Am I letting personal problems influence how I treat my work and team?

This is number one on my list, because I find it the most difficult.

Q. Am I sliding toward burnout?

I try to take a proactive approach to preventing burnout. To effectively lead others, I know I must first take care of myself. If I am not at the top of my game, how can I expect to inspire or guide others toward theirs?

Q. Am I reacting or responding?

It is easy to look like a fool, damage a personal or professional relationship, or make a technical mistake if you let emotions take control. To avoid reacting, I try to limit my multi-tasking, get six or more hours of sleep, and pause before responding. I respond as soon as I can emotionally divorce myself from an issue. When addressing a serious problem, or if someone is clearly upset, I prefer to avoid written communication – e.g. emails, IMs, and texts. I have found that written words can be more easily misinterpreted than spoken ones. Open and direct in-person talks or a phone call are my go-to methods. I then use an email to clarify and follow up on a verbal discussion.

Q. How much am I complaining?

“Ugh. I hate designing emails. I have to support five versions of Outlook!” Imagine if I made a comment like that in front of my team and then, weeks later, had to train them to do this very task and face these very issues. They are going to walk into the training session with a biased view and expect to hate any related assignment. I am setting up them and myself, as a manager, for failure. Rather than voice serious complaints in front of my team, I do my best to keep comments lighthearted and find actual solutions.

Q. Have I talked negatively about colleagues?

It does not matter if the subject of the conversation is your direct report, an intern on another team, or company leadership. If someone starts to talk negatively, not just critically, about another employee at the company, I usually attempt to shift the conversation or walk away. Negative gossip is poison. It can kill a group’s morale and eviscerate the trust others may have placed in you as a leader.

Q. Am I caring without becoming too much of a friend?

I make it a point to never become close friends with anyone whom I have the ability to fire. In my mind, this is up there with wisdom like “do not date a co-worker” and “never go into business with a significant other.” Sure, it works out in some cases, but you are taking a significant, unnecessary gamble. Your best intentions can blow up in your face. I have witnessed it happen. Why go down a road of potential self-sabotage when you can easily avoid it?

II. Individual and team development

Hire the right people

My top priority as a manager is to start with the best team members possible and pass over “B” players.

I achieve this through a rigorous candidate assessment process.

After a design portfolio screening, my main goal is to answer two questions:

  1. Does she have a history of getting shit done?
  2. Is she sharp?

I came across this strategy years ago in a blog post by Joel Spolsky, CEO of Stack Overflow. Five full-time hires later, I can confirm that it works quite well.

Other key candidate assessment questions that factor into my hiring decision include:

  • Is she an all-star no one yet knows? I want to hire candidates who have not yet been the best but have the potential. A similar approach is to hire people who are going to "punch above their weight-class." This is relatively easy to figure out if the answers to my top two questions are a resounding YES.
  • Does she possess highly-relevant interests and skills? Is this candidate likely to enjoy the work we are going to assign her? Project-interest alignment is key to keeping morale high.
  • Is she a good cultural fit? Will this candidate, who describes herself as a "rebel" at her last job, be able to step up as a strong team player when necessary? Getting cultural fit right is always critical, but it is even more important if you are a startup like Industry Dive was when I first started hiring.

Conduct quarterly performance evals

In order for a performance evaluation to serve a useful purpose, I believe you must first have clearly defined individual, team, and company goals and performance expectations.

That is the baseline.

After you have that criteria established, you can use a performance check-in to praise good work and recommend areas for further improvement. This can also help an employee understand annual salary decisions.

At Industry Dive, our performance evals work like this:

A direct report and a manager receive assessment sheets. The direct report self-assesses and emails the sheet to the manager. The manager fills out a similar assessment sheet about the direct report. The pair then meet at a scheduled time to go over both assessments. The reviews are mainly performance focused – where are you “rocking it” and where do you need to continue to grow.

How the in-person portion of an eval is conducted is left up to each manager.

My own approach looks like this:

  • Assess progress on development issues from the last quarterly performance eval. Were all of those issues properly addressed? If not, what do we need to do differently this next quarter? How can I, as your manager, help?
  • Assess current development issues. I ask the employee to be specific when listing areas for improvement. Then I make sure we have planned a few practical steps she or I can take to address each issue.
  • Give praise for hard work and wins. I ask the employee to talk about key accomplishments. I then fill in any gaps and point out areas where she is doing an awesome job.
  • Assess myself. I ask the employee to list specific ways in which I can be a better manager to her.
  • Open the floor for any other questions.

Conduct quarterly individual and team growth check-ins

In the fall of 2016, I started a quarterly “coffee check-in” with each team member to talk to them about their career interests and team growth.

I made clear that this meeting was not a performance discussion. The purpose was to get out of the office and chat in a more relaxed, one-on-one setting. I quickly found that team members were more open in their feedback in these casual sessions.

To help guide the check-in conversations and more easily compare notes between team members, I created the following set of questions:

  • Where are you going? The design career direction(s) in which you want to be moving
  • How will you get there? Concrete steps you can take here at Industry Dive to help you advance your design career
  • What are we doing well? Aspects of team or project workflows or dynamics you love
  • What can we do better? Aspects of team or project workflows or dynamics that are frustrating / pain points
  • How can we grow? Ways our design team can get stronger (things like competitive analyses of other design teams, book readings, events, etc.)
  • Anything else you want to talk about?

After the check-in, I immediately wrote up what I heard in an email and sent it to the team member. The email asked the employee to confirm that I heard her correctly and gave her the opportunity to add anything we might not have covered.