The credit belongs to the man… who at best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who know neither victory nor defeat. – Theodore Roosevelt

Sooner or later, every team member runs into a dilemma. They rarely talk about it with their teammates. They’ll think about it as they ride the train to work, as they pound out the miles on the exercise bike, as they stand in the shower for that extra 48 seconds before dashing into their day.

It’s the Trust Dilemma. The quandary looks different depending on the circumstances.

  • Should I give up budget or headcount to my teammate or grab as much as I can for myself?
  • Should I say what I really think in this meeting or hold back?
  • Should I invite debate about a key decision in our team or should I cut others out by lobbying the leader privately?
  • Should I assume the best about what happens when I’m not in the room or insist on being in meetings so that I can hear what’s really going on? 

That’s because “Can I really trust these people?” is one of the questions every team member is always asking. It’s a version of the question, “Am I in or out?” which bounces around everyone’s head in any group. 

One of the biggest reasons to invest in a team is to achieve something important together that none of you could achieve on your own. If you can achieve your most important goals solo, don’t bother with a team. Teams are a lot of work. They’re messy. They involve *gasp* people and feelings and many factors we can’t control. Perhaps most important, it takes a huge time investment to get them right. So if you can do your amazing thing without a team, go for it.

But many of the visions that get us out of bed in the morning – reimagining an industry, creating an exceptional organization that both generates profit and changes the world for good, or scaling up a high growth organization – require a team. And teams don’t work if people hold back. They only work when team members entrust themselves to the others.

There’s risk in going all-in on a team, particularly risk of disappointment when you trust someone to do their part and they fail – or worse yet, don’t even try. Or the risk of making a sacrifice for the team and others not reciprocating. Or risk of betrayal when you assume someone is telling you the truth about their intentions only to find out they were quietly doing the opposite. 

trust your teammates

When you think of it that way, being gun-shy is pretty rational. It’s no fun to be the one who climbs out on the limb, only to look back and see everyone else holding back, maybe even chuckling at your adorable gullibility.

This hesitation is reinforced by one of the most common narratives in our world, taught to me by Mr. Angel, my high school physics teacher. “No one else is going to look out for you, so you have to look out for yourself.”  That message gets deep into us, making it seem crazy to trust others to have our backs. And that “we have your back” sense is the essence of a really connected, effective team.

READ: How to Become the Best Version of Yourself As a Leader

You wind up getting stuck in the middle. On the one side is Mr. Angel, cool and detached and realistic.  On the other side is the part of you wanting to be part of something exceptional, and knowing that this kind of team does happen even if only rarely. 

The I-want-to-do-something-unusual part of you asks, “Is this group of people a normal, boring leadership team or is it exceptional?” 

Mr. Angel bets on them being your basic self-interested nightmare. 

Your response to this dilemma matters. No decision is still a decision – in this case, a choice to hold back, protect yourself, and in the process starve the team of your best contribution.

Since “undecided” isn’t a real option, you have to ask yourself a simple question about the risk: Is it worth it? Is the potential upside of the vision you’re pursuing together worth taking the plunge?

If it’s already worth it, ask your Mr. Angel to step to the side and get busy investing yourself in the team despite the risk. 

If it’s not yet worth it – or if you’re unsure – you have several options:

  • Increase the upside potential. If the shared goal of the team doesn’t move you enough to take the trust risk, challenge the team to go for something bigger, more important, more noble. Shoot for something that would get everyone’s hearts racing because it’s from deep inside you, something all of you would rather fail in attempting than never have striven for.
  • Decrease the downside risk. Try testing your team a bit before trusting them completely. “First little things, then bigger things,” is a maxim worth applying here. Start by giving your teammates a chance. Explicitly talk about your team ground rules and see if people abide by them. When (not if) someone flubs up on a ground rule, gently but firmly bring it up. See if that teammate and the team as a whole listens to you and takes your concerns seriously. Don’t expect perfection, but expect seriousness and openness and an authentic concern for the wellbeing of the group. 
  • Call the question. You’re within your rights to ask the team, “Hey, what kind of team are we actually going to be? Are we a team of rivals, basically playing out a competitive reality TV show until one of us emerges victorious? Or are we a team of allies where we have each other’s backs?” You may need to be painfully specific with examples of how this choice plays out around budgets and decision-making and recognition. Prepare for some squirms here because you’re making an implicit topic very explicit. But you’ll probably get some thanks from other team members who are thinking the same things and value the clarity.
  • Find a new team. It’s possible you’re saying to yourself, “I’ve given this group of people months and years of tests and they fail them far too often and far too casually. I’d like to trust them, but I can’t honestly imagine taking significant risks with them.” In that case, you’ve probably come to the end of the road with this team. It may mean leaving the organization or, if that isn’t an option, simply investing your best energies in another team in the company until something fundamentally changes in your leadership team.  


All of these moves involve risk. You know by now there are no risk-free moves on the way to shining brightly.

For your own sake, don’t put on the act of being a team when you’re not. That’s what typical, boring teams do, suffering and pretending while everyone knows it’s a charade. Go for something exceptional, something that demands you take a risk. That’s what your customers and employees and partners really need from you. That’s what our world needs from you.

Be Bright