How to know when you are ready to expand your career

“There may be nothing I’ve seen wreck the careers of high-performing, hardworking people more commonly than stepping into a manager role the person isn’t ready for,” tweeted Kieran Snyder earlier this month. The CEO of linguistic analysis firm Textio then follows up this with some very cogent remarks about knowing when to take that leap into management that really resonated with me.

This is because I faced a similar circumstance in my own career back in 1990, when I took the job to run Network Computing, a brand new computer publication. I have often mentioned that decision as a pivot point in my professional life in these essays, At that time, I was managing a group of about a dozen editors for PC Week — and this would be a big promotion to running an entire publication, hiring its entire staff, and learning how to get the magazine from words to a coherent whole. It shaped the rest of my career, to be sure.

I also addressed this topic a couple of years ago in this post about whether super coders should take the next step into management. It is worth reviewing that piece and listening to a discussion with Jaya Baloo and Troy Hunt on the subject.

Snyder lays out four important questions you need to ask yourself whether or not you are ready:

  1. Can you communicate complex expectations clearly? And behind this question is also holding people accountable — and avoiding eventual disappointments — for these expectations too. Even when you know this, it is still hard to achieve. “This is an issue I have faced, and often management fails to set clear expectations,” said Alan Elmont, who has been a recruiter and staffing professional for decades. “This has been particularly an issue with small companies or mid-sized companies that are growing too quickly.”
  2. Can you engage and mange conflicts well? Being fair in these fights is more important that being well-liked.
  3. Where do you fit in the scale between being a hero and being predictable? “Managers mostly do hero work to compensate when their team isn’t delivering,” she says. That could be caused by a variety of failures, such as unclear feedback or expectations or poor solutions delivery — or a combination.
  4. Finally, do you have the right combination of technical skills and a solid functional foundation to properly lead your team? That is a tough one to dispassionately assess, either by yourself or with your prospective hiring manager.

Now let me take another moment from my career when I got a job to run another publication. It was a major failure, and because I couldn’t do any of the first three things that Snyder mentioned above. I barely lasted a year there before being fired. I should have spent more time understanding the lay of the landscape and the management style of my eventual boss. Now, this happened years after my Network Computing anecdote, so you would think being older and more experienced I would have spotted the danger signs. But no, I was too caught up in the thrill of being chased for a new job. Live and learn.

While on the topic of career development, I had an opportunity to talk to a group of mid-career folks who are considering jobs in cybersecurity this week. You can see my slides below, and some of the issues that we discussed.



One thought on “How to know when you are ready to expand your career

  1. David, you never cease to impress… and inform, and inspire, and thought-provoke. Love this post. There’s so much more to leading a team than being good at what the team is charged to do. I’ll be saving this one for further reflection. Thank you!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.