It’s stifling enough to accept our own failures and limitations in the ever-bustling world of entrepreneurship. But dealing with the failures of our teammates can prove to be far more stifling. Once upon a time, when members of my team failed to meet their objectives, I often went silent and would say something like, “It’s alright — don’t stress. I’ll take care of it.”

I would always have a hunch when they felt bad, and I didn’t want them to feel any shoddier. Over time, I ended up with a heavier load on my platter. The team stopped using their initiative because they knew that I’d bear the slack – which resulted in me feeling overwhelmed.

In my heart I knew I was being too easy on them, but what was I meant to really do? Yell to the top of my lungs? How would it be possible to be hard on people if you have a big heart?

Fight or flight?

About a year into my previous venture, came about my calling– I was raising money from a number of various investors and I’d sent an outdated financial model as part of the due diligence. When I opened my emails, each of the investors had responded with a series of hard-hitting questions about the model. My stomach churned.

Sweat began to beckon me. A surge of adrenalin and urgency rushed through my brain. What was I going to do to solve this issue? And more significantly, how could I guarantee that it never happened again?

Why “oh s**t” moments are key?

Now picture what would have happened if the investors had said something like, “You don’t have to worry about the model. We’ll fix it later.” Would I have felt the same sense of urgency or accountability? Would I have been as proactive?

Looking back on my career, the amount of those “oh shit” moments has had a tremendously positive effect on me. They’ve strengthened me in the face of failure, pushed me to take more responsibility for my actions, and propelled in becoming a far more gung-ho planner.

The trickling of the sweat on your forehead; That is part of taking responsibility. In attempts to lessen my team’s discomfort about failure, I ended up reducing their sense of responsibility while at it. I, therefore, learned that if I wanted my team to feel responsible, I needed to get acquainted with their discomfort.

By stopping my questions when it got uncomfortable, I wasn’t helping my team to grow and learn.

Giving your team an “oh s***” moment

In the reference above, the investors didn’t yell at me, blame me, neither did they make it personal. Rather, they just asked tough questions that made me profusely aware that I had made a mistake.

Questions are like blinking a light into a particular area of your mind. Sometimes, it can reveal a monster lurking in the shadows — something you’ve forgotten about or an assumption you’ve made. Asking hard questions is part of what the accountability game is all about.

By stopping my questions when it got uneasy, I wasn’t quite helping my team to grow and learn.

Here are some of the questions I would ask my team after a failure:

• What actually happened?
• What is the impact of this?
• What choices did you have?
• What could you have done to avoid this?
• What do you learn from this?

I’m no longer tempted to answer for them, and I try to hold the silence long enough to encourage them to think before they speak.

The early sweats that matter

It’s indeed easy to let new joiners off the hook for their mistakes. We know that everybody wants to make a good impression early on, and we might justify our leniency with the train of thoughts like, “They’re probably just familiarizing with things. I’ll give them the benefit of the doubt.” However, missing these early opportunities to ask tough questions makes it harder to hold people accountable later.

When I was hiring my last sales team, a new sales exec showed up on his first day completely unprepared. I brought him aside and asked him to explain how he’d prepared for his first day at this new job. I kept probing him to further reveal his ill-preparation. I concluded by saying, “Listen — if you’re not better prepared tomorrow, you’re not going to last until the end of this week.”

I recall noticing a sweat take over him. But what happened next was an incredible transformation.

He had easily the best second day of anyone in the company by far. And six months in, when it was promotion time for members of the sales team to managerial positions, he was without a doubt the best choice.

Early feedback had a lasting impact on him. This had led him to take his job far more seriously and thrived as a result.

Seize the discomfort

To be an epic manager, you have to get comfortable with allowing your team to handle the pressure. Delegating responsibilities is how you help people grow and learn.

If watching other people struggle is not your thing, re-think of it like this: It’s an opportunity for you to step out of your comfort zone by getting your team out of theirs.