Trust Your Team or Hire People You Do

By Poornima Vijayashanker

A couple months ago I sat down with a startup founder who was also the CEO of the company. He said he felt really overwhelmed and had too much on his plate. So I asked him to list out EVERYTHING that was vying for his attention, including personal tasks.

Here is the list he came up with:

• Hiring a new front-end engineer
• Hiring a new designer
• Closing 3 enterprise sales customers
• Creating a new sales deck to pitch the 3 enterprise sales customers
• Prospecting 100 new customers each week
• Answering customer support emails
• Making a list of investors to reach out to
• Creating a pitch deck
• Picking up and dropping off his son at daycare
• Playing ultimate frisbee twice a week

Then I asked him what his goals were, emphasizing both personal and professional goals:

• Spend time with his son
• Stay healthy
• Close 3 enterprise sales customers
• Close $1M in funding by September

Those looked like some clear goals to me. So then I asked him why he needed to be doing all those other things. He realized he didn’t, and we put a plan together for him to delegate most of the work to his co-founder. He agreed to just focus on fundraising and closing the existing customers in the pipeline, but nothing more. It would also give him some free time to spend with his son and get some exercise.

About a month went by and the founder invited me to his office to meet with him. When I arrived he was in a meeting, so in the meanwhile, his co-founder took me out for tea. We got to talking, and I asked the co-founder how the startup hiring and recruiting was coming along and if he needed some help. The co-founder said that he and the founder were working on it, and they were pretty close to closing a designer but still struggling a bit to find a front-end developer.

Then I asked about sales. Again the co-founder said that he and the founder were working on closing the 3 enterprise sales customers, and had been actively prospecting for the past month. They had about 125 prospects.

Next I asked about fundraising, and the co-founder responded that the founder had just been so busy the past month with sales and recruiting that he hadn’t gotten around to making the investor list.

We wrapped things up and went back to the office.

I sat down alone with the founder. He looked tired.

When I asked him how things were going, he told me the same things that his co-founder had told me, and he added, “I know we had talked about fundraising Poornima, but I’ve just been too busy.”

I asked, “Is fundraising no longer a top priority?”

“No, it is a priority, it’s just that there are other things that need to get done.”

Since I hadn’t gotten through to this founder the first time, I decided to up things a notch, and asked him, “Do you trust your co-founder?”

He said, “Absolutely! We’ve been friends for 10 years and working together for the past 4. I trust him 100%.”

“And do you think he’s capable of prospecting for customers and recruiting employees?”

Again the founder said yes. So then I asked, “Does your co-founder not like doing these things or has he pushed back?”

The founder responded, “No, he’s happy to help.”

“Then why are you still involved in prospecting and recruiting?”

The founder admitted that he had a hard time delegating, and that his co-founder had brought it up a couple times. While he did trust his co-founder, he felt the need to still be involved. He didn’t want to think he was abandoning his co-founder.

I told him that’s fair, but that if he continued to be involved, 2 things were likely to happen:

1. His co-founder would feel like the founder didn’t trust him, which would strain the relationship.
2. The company would miss its goal of fundraising by September.

To make things crystal clear this time I told him that he needed to trust his co-founder and his team with the startup hiring process, and if he didn’t, then he needed to hire people that he does trust to get things done.

One of the reasons co-founders split and employees leave is because they feel like the founder just doesn’t trust them to do their job. It’s caused by the founder doing things like:

• Micromanaging projects instead of just setting up clear goals for employees and then moving on to focus on what’s on their plate.
• “Railroading” decisions by overturning someone’s original decision or making all the decisions for them.

Over time, smart and high-performing employees will feel like they have no say and their only option is to leave, because they aren’t being heard and trusted.

Others will start to question their own abilities, causing them to stall on projects because they are waiting for someone else to make the decision for them or “approve” of their work.

Neither is a positive outcome.

The founder didn’t want to lose his co-founder and asked me for help. Together we set up some clearer criteria for good delegation.

What does trust look like?

Set clear goals for teammates that do not conflict. The founder and I set 3 goals for his co-founder. Goal #1 was to close the designer. Goal #2 was to continue to look for a front-end engineer and leverage advisors like myself to make that happen. Goal #3 was to continue prospecting and to work on deals that were under $25,000 alone. If the deal was more than $25,000, like in the cases of the 3 enterprise customers, then he’d alert the founder and ask for help, but still be responsible for closing it.

Set clear goals for the leader. The founder’s only goal was to start working on fundraising, and there were plenty of tasks involved to keep him busy.

Let people make mistakes! The founder was, of course, worried that his co-founder may or may not be able to close the 3 enterprise customers. I asked him if the business would be in jeopardy if the deals didn’t go through and the founder said it wouldn’t. I also asked the founder how many deals had he lost in the past year, and he acknowledged that he had lost deals himself and was holding his co-founder to an unfair standard of success.

I told him that he needed to give his co-founder the benefit of the doubt, and even if the co-founder screwed up ALL the deals, the business would sustain itself.

Giving his co-founder the freedom to try and fail would be a good lesson – far better than losing him because of a perceived lack of trust.

Stay tuned for next week, when we’ll talk about what employees can do when they’re on the receiving end of a hesitant delegator!

In the meantime I want to learn from you! Whether you’re working at a startup or larger organization, you’ve probably had a similiar experience: someone didn’t trust you to take the lead. Or, maybe you didn’t trust someone, I know I’ve done that plenty of times and I’m still working on it! I want to know: What you did to resolve the situation?

Let me know in the comments below!

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