Question Your Leaders and Dive in - David DeWolf

Question Your Leaders: Why It’s Better to Dive in than Walk Away

800 531 David DeWolf

A couple of weeks ago I found myself perplexed. A leader that I have profound respect for – and consider a mentor – had approached me about doing business together. This is someone I look up to and would have loved to work with. Of course I couldn’t wait to say yes.

As our conversations continued, I was put off by a couple of details associated with the deal. I couldn’t understand why this person would conduct business this way. Something wasn’t adding up.

Luckily, I’ve been in this position before and have learned the hard way not to leave my questions unresolved. Ignore the “gut feeling” and you risk everything from being duped to ignoring a simple warning sign that motivations are misaligned. Both can end in disaster and destroy a relationship, regardless of how much you trust the person you’re doing business with. On the other hand, simply walking away might be safe but prevent you from a unique opportunity.

So, I dove in. I had the hard conversation. I asked about my concerns and expressed my fears. I spoke to a mutual friend that had entered into a similar arrangement and he helped me understand the reasons why these details made sense, at least for this leader and in this situation. There was information that I didn’t understand.

Only time will tell whether I fully embrace the approach. I’m not convinced that it isn’t extreme. That said, I understand its purpose and am open to the reality that I just might learn something from someone who knows more than I do. Regardless, I’m not able to move forward, with peace of mind, with an opportunity that has the potential to be monumental.

How often do you question your leaders? Do you dive in to understand, or do you simply walk away or risk getting burned?

The reality is this:
  • Leaders often have more context and information than you do. Seek to understand before making a judgement.
  • Leaders don’t expect you to follow blindly. Seek the clarifications you need to be to be comfortable.
  • Leaders are human. They make honest mistakes. Strive to be transparent about your hesitations, perhaps they are wrong.
  • To get ahead, you have to take smart risks. Don’t risk getting burned, risk the hard conversation.