How do I trust my Co-Founder again after he drops the ball on an important meeting?

How do I trust my Co-Founder again after he drops the ball on an important meeting?

Occasionally my readers will send me requests for topics they would like to see me write about on my blog. The following is a question from a reader.



Dear Tara, 

My company is going through a rapid growth phase and I had to delegate an important meeting to my because I couldn’t be in two places at the same time. The meeting was with a big client and it was a relationship I had been working on for a long time. I feel like my Co-Founder/COO knew how important it was for the company that this meeting go well so I was extremely disappointed and angry when I got out of my meeting and found a voicemail from the client asking me if everything was okay because my COO missed the meeting. I was able to reschedule the meeting, but now I feel like I have to do everything myself if I want it to be done correctly. How can I trust my second in command to handle situations like this in the future as the company continues to grow?

Growing Pains

Dear Growing,

It is such an exciting time in your business knowing that you are about to reach a new level. You would not have gotten this far if you didn’t have a dedicated team of people working together to push the company forward. It is normal to feel like there are not enough hours in the day to accomplish everything on your “to do” list, so please take a moment to acknowledge yourself for finding solutions through delegation.

Of course, hindsight is 20/20 so you can look back and say things like, “I should have never trusted him to take the meeting for me.” Instead of shaming yourself for not doing everything yourself, try asking yourself “How can I close the communication loop on important tasks I delegate to others in the future?” because chances are you are going to have to delegate things to other people more and more as your business grows.

While you can’t change how you reacted to this situation, you can learn from it moving forward.

First, recognize that you both had the best intentions. Your COO intended to take the meeting and make it a success. At the same time, maybe you intended to let him take on a bigger role so he could grow with you and the company.

Second, think about what you really want to accomplish. I don’t think you want to belittle him or make him feel bad for dropping the ball. What you want is for him to take ownership of the company the way you do. The company is your baby and you would stop a moving train to protect it. You want everyone in your company to be that passionate about your baby.

So, how do you do that?

You are on the right track with wanting to delegate things and while delegation came from a place of necessity this time because you are overwhelmed, in the future it can come from a place of allowing other employees to feel accountable for the success of the company.

Here are some steps you can take in the future to ensure that tasks are delegated successfully:

1.     Understand your priorities and communicate them consistently. This meeting was extremely important to you and it won’t be the first or the last time you have to delegate something that is critical to the development of the business. One way you can communicate this is by color coding a shared calendar. For example, you can put high priority tasks in red, secondary priority tasks in yellow, and lower priority tasks in green. Another way to communicate priorities in writing could be in the e-mail subject line. P1 could mean top priority, P2 secondary priority, and P3 low priority. Find a system that works for your organization.

2.     Once you establish the various levels of priority, define what each of them means. How quickly do you expect a top priority task to be completed? Which employees within the organization is it appropriate to delegate a top priority task to? How will you close the loop of communication? For low priority tasks it may be appropriate to close the loop by sending an email that says, “Done.” For high priority tasks you may want to schedule a meeting on your calendar to debrief right after the task is set to be completed.

3.     Be open to teaching. Most skills can be learned, so don’t be afraid to delegate something to someone who may have never done the task before. Be sure you take the time to ask them if they understand how to perform the task, give them the opportunity to ask questions, and ensure they understood what you were asking them to do by having them teach it back to you before you perform it.

4.     Check-in with the person you’ve delegated the task to. In this situation, you delegated a high priority task. The morning of the meeting it would have been appropriate to check in with your COO and ensure that he was prepared for the meeting. In other situations you may want to check-in periodically to make sure the tasks that have been delegated are moving forward. The key to checking in is to avoid stepping in to tell your employees how to perform the task. Trust them to execute it.

5.     Close the loop. Be sure you have a system and structure for how you will execute #2. During this time it is also appropriate to ask your employee what he or she thought went really well and what the opportunities for improvement are.

Got a question for Tara? Post in our Facebook or LinkedIn groups for more help.