It was on St. Patrick’s Day seven years ago that I first had the idea for what would eventually become Geckoboard. And no, I hadn’t drunk too much Guinness. ;)

From the early days of defining and building the first prototype to now managing a team of 35+ people, I had to figure a lot out the hard way. A big thing has been figuring out when and what to delegate. It’s been a challenging process.

Since delegation is a common struggle among founders, I thought I’d share some of what I’ve learned (and am still learning).

Recognizing the need for delegation

In the early days, I did everything myself. I had the drive and the energy because I was motivated by the product idea. I wanted to be the one who brought this product idea to the market, as I felt it needed to exist.

Initially, this was beneficial to ensure the product was true to the vision I had for it. Looking back now, I can see the trust issues surrounding the ‘delicate flower’ that was my idea.

But I soon realized it wasn’t feasible to continue doing everything myself. There was just too much. If you’re building a company for the long-term, you have to wake up and realize it’s unsustainable to work insane hours for an unlimited amount of time.

Like many founders, I have a family and that part of my life would’ve suffered if I’d continued along this path. I didn’t want that.

Letting go and overcoming trust issues

One of the biggest challenges with delegation is letting go and trusting another person enough to get the job done. I struggled to entrust anyone with my idea. But ultimately, I had to take a leap of faith.

I also had to trust my own process for hiring the right people. This meant being clear on what help I needed and the type of skills I was looking for. It helped to hire people who had empathy towards this - people who understood this idea was my baby and were willing to take great care in developing it.

Although difficult, relinquishing control is incredibly liberating and empowering. I’ve worked with micro-managers before who were constantly looking over my shoulder and trying to preempt everything. It was stifling.

Because of this experience (and how much I hate it), it actually felt great to say “Here’s the remit. Let’s be clear about what we’re trying to achieve here and let’s keep the communication going, but this is yours - go do it.”

Good indicators it’s time to begin delegating

Aside from burnout, there were two main indicators that showed me it was time to start delegating work.

The first was having too many decisions to make and not enough hours in the day to make them. Nobody is great at everything and time is limited, so focus is important in every startup. The question then is what can I contribute in the limited amount of time I have that’s going to have the maximum impact? That necessarily rules out lots of low impact tasks.

The second indicator was a lack of capability. This one requires a level of intellectual honesty. I had to be real with myself - “I’m not the best person to make this decision because I don’t have the grounding in this area.”

Unfortunately, there’s no cookie-cutter way of figuring this out since each founder’s strengths will vary. But be honest with yourself, know what you aren’t good at, what you are good at, and how you can most effectively deploy your skills.

Any area where you’re not adding the greatest amount of value the company could be getting is grounds for delegation. Having someone who can come in and spot problems or opportunities way before you do it the first time is invaluable.


What to delegate in a growing SaaS business

Deciding what to actually delegate depends on the background and type of founder.

For any SaaS business, though, there are a few essential building blocks: product (including engineering, design, product management), customer support, marketing, and, in some cases, sales. It’s unrealistic to expect a single person to be good at all of those things.

Personally, I’m a product-centric founder. It’s where I get my energy and creativity. But I’m not so arrogant to assume that by focusing solely on the product a business will emerge.

The two key areas I struggle with are customer support and marketing, even though I spent hours doing both in the early days. I didn’t want anyone else defining the relationship with our customers because I wanted to provide the kind of service I would want if I were the customer. (This ties back to those trust issues I mentioned earlier - letting go is a process!)

But once I finally hired our VP of Customer Success, Luis, he took a completely different approach to building and organizing customer support than what I was doing. His expertise allowed him to transform our customer service from average to what I would say is best in class. His approach was far better than anything I could have done because this is his specialty.

For any SaaS company, it’s definitely worthwhile to hire someone like Luis with expertise in customer service as there will always be product questions to answer.

I also recommend hiring someone with marketing expertise if that’s not one of your strengths. I don’t have the skillset or rigor to cut through the noise and put together a plan from something that seems ephemeral. But it’s wonderful to watch our VP of Marketing, Simon, do it so well.

You can work hard and read all the books, but unless you’ve seen it and have the battle scars from doing it, there’s never any substitute for delegating to someone who has the expertise.

How to delegate...

Knowing when and what to delegate is important, but it’s only the first step in building your first management team, moving away from the hands-on work, and growing a sustainable business.

Learning how to delegate has also been a big part of the process for me, and an equally big learning opportunity (spoiler: I’ve made plenty of mistakes along the way). I think it deserves its own post, so I’ll follow up next week with some thoughts on how to delegate.