Last week, I wrote down lessons I’ve learned on what and when to delegate. Today, I want to talk about some of the hard lessons I’ve learned about how to delegate. I’m still not perfect at this, but being CEO has forced me to get better at it over time.

Finding the time to delegate is hard

Let’s be honest, it’s REALLY hard to find the time to do anything. As an early stage startup, you’re under constant pressure to do things immediately. Investing in the long-term by handing-off parts of your job can seem like a luxury, not a necessity. I’ve made plenty of mistakes in this area, for sure.

The question is: are you willing to take the time to invest in the future of your business knowing full well that it will take time - and even if you put in that time it won’t necessarily work out?

I’ve learned that if you’re building a company to last, then you must be willing to take this time.


Hire before you need it

In the early days, I was able to bypass some of the time crunch by hiring incredibly driven people. These are individuals who say, “This is a neglected area at the moment, I want to own it and here’s what I’m going to do.”

They have a sense of ownership.

But as the company grows, there are few if any “unowned” areas of the business and you’ll need to be comfortable handing off existing areas. The most important thing as you do this is to hire before you absolutely have to do it.

I had to be honest with myself about the competencies I needed and learned that bringing those individuals in earlier was better, even if it was a few months early. It cost us more runway, but I actually bought myself extra time to get new team members ramped up.

You can’t expect someone to be productive from day one. Build in some buffer time, and they’ll be more productive in the long-term.

The follow-up conundrum

Once I delegated various roles or tasks, following up became a very difficult balancing act. I didn’t want to hand someone a job to do and then be looking over their shoulder the whole time.

One of the mistakes I’ve made is delegating an atomic unit of work and saying, “Off you go, see you later.” The combination of people being afraid to ask for help and my aversion to micromanagement created a situation where we were really far down the road with divergent ideas of what someone was actually doing vs what they were supposed to be delivering.

But I’ve realized that I can be helpful without micro-managing.

In order to get back on track in a situation like this, the first thing was for me to be honest - “I didn’t handle this as well as I should have.” The worst thing I could have done was to start throwing blame around. If there’s a problem with communication, I have to take my responsibility for that.

Ultimately, if I’m delegating work - it’s incumbent on me to ensure it’s properly communicated.

Processes that help with follow-up and minimize frustration

Effective delegation comes down to two key elements: trust and communication. If trust goes out the window, you’re micromanaging; if communication goes out the window, there’s a massive divergence in expected outcomes.

The best thing I’ve found is to have clearly defined goals and outcomes and then talk about progress toward them regularly. For me, this means weekly 1:1s with all my direct reports. These regular check-ins allow me to remove blockers and provide the necessary support for my team to accomplish their work.

I also take an interest in everything that goes on. One of the reasons I attend our daily engineering stand-ups is so I can see the cadence of work and understand the challenges people are facing.

Shifting from product person to CEO

When I initially thought about starting a business, I was mostly blind to how I was going to actually lead the business. I came from a product point of view. I felt strongly that this product needed to exist and I wanted to be the one to help bring it to the world.

I didn’t think about the life support for a product which is essentially people - great people and a great environment. I have no experience with it and it’s intimidating as hell.

Back in 2012 when we were fundraising, I hit a crossroads between owning the product and being CEO. I knew we had to build up momentum to raise the money we needed, so I spent nearly 100% of my time talking and meeting with investors. Within three weeks I’d spoken to around 60 investors.

When you attack a project like that, something has to give. For me, this meant relinquishing control of the product.

Honestly, Geckoboard wouldn’t be here today if I hadn’t released some control over the product. I had to get real with myself, “You’re no longer the product person here. You’re no longer the person who can oversee and control every aspect of this.”

Of course, I still provide input, but I can’t own the product like I used to.

It isn’t easy to switch focus from where you feel your heart is to where your head needs to be. It’s fraught with difficulties. It’s challenging and sometimes painful.

Making that shift possible

Though it hasn’t been easy, there are two things that have helped (and continue to help) me make the shift from product person to CEO.

First, I focused on hiring great people. I’ve hired people who are more competent than me. If Geckoboard is going to thrive and continue to grow, I need to bring on people who are smarter and more effective than me.

Second, I pushed myself outside of my comfort zone, even though I found it very difficult most of the time. A few things that help in this regard include surrounding myself with better people, throwing myself wholeheartedly into learning something new, and listening to people who’ve been in a similar situation. That’s why we launched our Secrets for Scaling podcast to help founders learn from other founders.

I’m lucky to have a team who is forward with feedback. It’s wonderful when someone comes up and says, “I think our vision needs to be clearer and here are some ideas for improving it.” Great! I know this is a blind spot and I want someone to push me in areas like this.

The truth is, I’m still coming to terms with being CEO. Some people get into the startup world because they love this aspect. For me, every day is a genuine challenge - a character defining challenge.

At the end of the day when I’ve looked at the last email, I think about all the things I could have done better. And that can be viscerally draining.

But creating a company that offers a product we’re proud of and is genuinely a great place to come to work every day is worth the challenge.

What challenges have you faced as a founder in delegating? I’d love to hear how you’ve improved your delegation skills in the comments!

PS. We’re hiring!