Management A path forward

Your Mid-Year Leadership Check-in

A satisfying aspect of the new book was I achieved the intended goal of providing actionable advice. After a brief introduction, I list the 30 specific practices you can start with today to improve different aspects of leadership. I then go onto to tell the story of how I discovered or refined that practice.

The reason this is satisfying is so much leadership advice is “it depends” advice. I’ve learned this during the Q&A sessions after a talk. I’ve just finished a 30-minute speech, and you stand up in front of 499 audience members and ask me a zinger. It’s a good synthesized question. It’s on topic. It’s specific, and about ten words in, I can tell it’s an “it depends” question.

The types of situations you’ll encounter as a leader are as varied as the humans who build them. Yes, your question strikes a familiar chord with me, but with that familiarity comes the experience that informs me that unless I understand the specifics of the situation, the value of my advice is suspect.

But I have to say something, so my advice moves to the abstract with the hope that if I describe the general problem space with equally general approaches that you’ll take those generalizations, combine them with your knowledge of the specifics of the situation, apply good judgment, and find a productive path forward.

High-level hard-earned advice and well-intentioned generalizations threaded through a good story were the first two books’ approach. I wanted to get you thinking about a problem space, and with that in mind, let’s pivot to your mid-year check-in.

It’s halfway through the year. We remain in unknown territory for most leaders as many of us continue our month-long work-from-home pandemic set-up. For me, I spent months thinking, “This is temporary. Don’t get used to it.”

I’m used to it. This isn’t temporary. It’s time to start thinking of how you will move forward as a leader in these strange times. To get you thinking about this problem space, I present ten questions.

  1. Are you a manager, manager of managers, or manager of directors?

  2. How long have you been in that role? The prior role?

  3. When was your last promotion, and what was your internal headline for that promotion? (Example: “Reliable manager finally gets the promotion to a senior manager after the successful release of X.”)

  4. Who are your credible sources of actionable feedback? What the most recent memorable feedback from one of these sources? Why was it memorable?

  5. What are your areas of strength? How do you know that?

  6. Where are you focusing on improving your leadership skills? Why?

  7. Have you identified your next role? If so, what is it, and what’s your current plan to get there?

  8. What’s your current most significant challenge with your direct reports? (A specific issue with one of your directs or an overall issue with all/many)

  9. What’s your current most significant challenge with your manager?

  10. What do you want to be when you grow up?

While I am intensely curious about your answers to these questions, that is not the point. These questions are designed to show you at least one essential truth about your current leadership role. What are you going to do with that truth?

It depends.

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3 Responses

  1. Tom W 2 months ago

    What do *you* want to be when you grow up? 🙂

  2. Gordon Milne 2 months ago

    1. I am a team leader, the first level of line mgmt in this organisation

    2. The entire 10 years I have been here. Prior to that, I was head of software (team of 4) at a small startup for 4 years and as an IC the 3 years before that.

    3. My last promotion was at my previous employment. The previous software leader left and I asked for the job. The CEO accepted me because I was the best person for the role at the time. I was certainly a safe pair of hands — did what the business needed, not what the devs thought was most interesting.

    4. My manager is my most credible source. He causes me to reflect on the way in which I am “seen” to do things, I am often perceived to be “pointed” in my interactions on technical matters. I like precision in technical discussion I don’t like hand-waving.

    5. Highly logical on technical discussion; strong empathy on emotional matters. I know because people choose me to discuss technical matters 0if they want an honest appraisal; they choose others if they want the approval of their idea. As for emotional matters, I get feedback from the face to the person I am having the discussion with.

    6. I am not focussing on improving my skills. I am reading books on the matter but more for interest than actional ideas.

    7. No, I have not identified my next role. Frankly, in my mid-fifties, the scope for advancement in my organisation is limited due to our poor financial performance. I have looked at positions elsewhere but have yet to get past the 1st in-person interview.

    8. Getting them to talk in the language of the domain instead of the language of the implementor. This carries over into our codebase which, at a high-level, can be suffused with implementation-oriented names instead of domain-oriented names.

    9. I have no problems with my manager. The only issue is how long it can take to “firm” up commitments on backfills for departed colleagues. We seem to take every departure as a reason to relitigate the need for that position.

    10. Goodness knows. Something to do with quality products from the inside out.