Leadership isn’t easy. It’s full of tough calls, people problems, and personal doubts. I’ve been there in combat, in business, and in boardrooms. That’s why I started this monthly Q&A: to offer practical, battle- and business-tested advice for the challenges leaders face every day.
Each month, I choose a handful of real questions submitted by readers like you and share my no-fluff answers. If you don’t see your question here, hang tight — I may cover it in an upcoming issue.
Let’s get into it.
I have a teammate who isn’t pulling their weight. When should I loop in the boss?
Only after you have tried everything and they are just not responding. You don’t want to bring this problem to the boss, unable to demonstrate that you have done your very best.
In terms of improving performance. Get to know the person deeply. What motivates/demotivates them? What fuels their anger? What constitutes an expression of their love? See my first book, It’s Personal, Not Personnel.
Everything feels urgent. How do you set priorities?
Setting priorities is a risk equation. “If I ignore this one does the ship sink? Can we recover?” If yes, the ship sinks, it must be a top priority. If we can live through the day — nobody gets hurt, it is not the beginning of the end — it is probably a lower priority.
Always return to your why, your vision — why you exist as an organization. Let this be the North Star to guide you.
My subordinate has been dealing with personal issues, and it’s starting to affect his performance. How do I approach this conversation?
Start with empathy. If you skip this step, you’ll be seen (and probably are) as a careless leader. Do what you and the team can do to help him, but find out what he is doing to overcome his issues. If it’s just a constant pity party, that’s not helping anyone.
This person ought to demonstrate the ability to get beyond their personal issues for the sake of the company’s mission and their teammates. You can show empathy and problem-solve in the same conversation. You are not being insensitive, just loyal to others and to the mission. You cannot be faulted for that.
Remember, you care — but the business (the mission, the customers) does not. It’s a tough line to walk, but you must, and they should be mature enough to understand.
What books would you recommend for learning leaders?
There are several, but three come to mind that really spoke to me:
- Multipliers by Liz Wiseman
- The Culture Code by Daniel Coyle
- Team of Teams by Stanley McChrystal
All great books on leadership and culture missing in many organizations today.
What’s one underrated skill every leader should work on?
Vulnerability. I never thought of vulnerability as a leader, though I was vulnerable. I felt I was just being human and humble. I was, but it was actually vulnerability. People flock to vulnerable leaders.
Brené Brown is the authority on vulnerability. She has great books and TED Talks that speak to this.
