10 Questions to Ask Before You Invest in Leadership Development

Let's do an offsite!

We're scaling fast and need our leaders to keep up - let's get some training and coaching in.

Why aren't we moving as efficiently as we know we could? Let's get some leadership training. 

Executives need to level up - let's get some coaching.

Many orgs turn to leadership training and development at pivotal moments - after crises, at the behest of the board, or when things just seem to be falling apart. Frankly, it's something orgs turn to almost as an answer to unarticulated questions around growth, performance, and goals. 

Regardless of the question, Leadership training and development seems to be the answer. The miracle cure. The magic wand. 

But more often than not, leadership development doesn't do much developing. 

Leaders might be on a high shortly after a program ends, and they go back to their companies perhaps trying to implement what they've learned, only to abandon it all and return to work as usual within a few weeks. A month later, nothing has changed. The leaders are back to the same patterns. The money is gone. The system, untouched. 

Why Leadership Development Doesn't Stick

Most companies invest in leadership development the same way they invest in software - they buy it, install it, and expect it to work. 

It doesn't. 

Not because the programs are bad, but because the system around the leaders hasn't changed. In the words of Dr. David Drake, "We often end up sending changed people back into unchanged environments. And we know which one wins that battle. It's not the person."

The 10 Questions

Answer these alone first. Notice which ones you can't answer without your team in the room. That's where the real work begins. 

1. What did we try last time, and why didn't it work?
2. What specific change in our business will we see if this works?
3. Do we know which leaders are operating above their level, at their level, and below their level, and have we said it out loud?
4. How do decisions get made today within each function?
5. How do decisions get made between function heads?
6. Where do we see leaders working around the system instead of through it?
7. Which dysfunctions does everybody already know about but no one is naming?
8. What will we change about how we work so that what leaders learn doesn't evaporate?
9. Who owns this program internally and do they have the authority to make it stick?
10. Are we willing to let go of leaders who can't or won't grow into the role, even the ones we like?

Most leadership teams can't answer half of these alone. That's not failure. That's actually the point. 

Leadership development doesn't fail because the content is wrong. It fails because the operating system and context around the leaders - how decisions get made, who has authority, what gets named and what stays unspoken - stays exactly the same after the workshop ends. 

The questions above are designed to surface that system. If you can answer them with your team in the room, you already know what to do next. If you can't, the conversation itself is the first move. 

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