Assessing Your Own Experience

• At this level, your coaching and mentoring are likely to come from people outside of your company. You no longer have a manager, you have a boss. Do you have a professional coach, either provided by work or paid for yourself? This is a good investment even if your job doesn’t pay for it. A coach can give you guidance and direct feedback, and unlike your friends, she’s paid to listen to you talk.
• Beyond a coach, how is your support network of peers outside of your company? Do you know other senior managers at companies in your area? A peer group helps you see what the job looks like at other companies, and is a place where you can share experiences and get advice.
• Do you particularly admire any technology senior managers? What is it about them that you admire? What could you be doing to be more like them, if anything?
• Think back to the last time you needed to change priorities for part or all of your team. How did it go? What went well, and what didn’t go well? How did you communicate the change to your team, and what was their reaction? If you were to do it again, what is one thing you would do differently?
• How well do you understand where your business is going for the foreseeable future? Do you understand the technology strategy that will help you get there? What are the critical areas of focus for the team, such as feature velocity, performance, technical innovation, and hiring, that need to evolve to reach the goals of the company? Where are the bottlenecks or opportunities for technology evolution to push the business forward?
• How is your relationship with the other members of the company’s senior leadership team? Which relationships are good and which are bad? What could you do to improve the bad relationships? How well do you understand the priorities of these team members, and how well do you think they understand your priorities?
• If I asked your team which executives you got along with and which ones you hated, would they be able to tell me without hesitation? When the CEO or the leadership team comes to a decision that you don’t agree with, are you capable of leaving that disagreement behind and supporting the decision to the rest of the company?
• Are you behaving like a role model for your team? Would you be happy to learn that people were emulating your behavior on a daily basis? When you sit in on meetings with your team, do you dominate the conversation or are you more interested in listening and observing?
• When was the last time you asked someone you don’t talk to regularly about his life outside work? The last time someone emailed to say she was sick and couldn’t come in, did you take a minute to wish her a quick recovery?
• What are the fundamental principles you want your senior engineers to be considering when they evaluate work and make decisions? Or, if you are focused more on organization than technology, what are the fundamental management principles you want your managers to be following when they lead their teams?