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How to set goals

We sit down with Maarten de Boo, co-founder and Chief Revenue Officer of Widget Brain to discuss how to set goals.

DISCLAIMER: This interview was recorded and introduced as a lecture for our free online 10-week program, StartupLeap. It has been edited for clarity purposes. Watch the recording for the full conversation.

Widgetbrain is an AI-driven scheduling automation for workforce or maintenance planning

This interview was recorded in collaboration with Erasmus Centre for Entrepreneurship

How do you approach goal setting?

At this moment, we’re scaling up, which means we’re setting up second and third layers in our company that require us to rely on people to do their own thing. For that to happen, we need to make sure they’re still doing the right things.


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How to do this, is to set measurable goals everybody is aligned on, but also realize you haven’t completely validated your value proposition yet. You also need to measure qualitatively.

You divide between process goals and goals that measure certain outcomes?

Measuring starts with checking if your team has taken the agreed upon steps and if those lead to results.

First of all, all teams, we have teams in the US, Australia and in The Netherlands, need to be self-sufficient. That means you have to discuss the right tasks they need to perform and make them responsible for achieving their goals.

Qualitative goals can be things like being able to give a demo or produce marketing content that fits the local market. Or being able to integrate with certain players in a local market. Teams need to be part of a local ecosystem. I can’t dictate from Rotterdam what they need to do in Australia if I don’t know the ecosystem.

Where to start?

It all starts with the big hair audacious goal. Where do we want to be at what certain moment in time?

Then you go back into your organization and discuss what you need to do to get to that goal and ask all disciplines in your team what they need to achieve this goal.

For example, how long do they need to get there, how many products do we need to sell, how many markets do we need to be in, how long does it take to implement products, or how long does it take to service customers, how many accounts do I need to address to get how many demos, to get how many offerings.

Then when all teams follow the road described, a certain payload follows, which you can translate to the amount of people you need. Which translates to the amount of money you need to pay them, to hire them, etc.

Important to remember is that there’s always a gap in time to bridge, so if you want to hire someone now, they still need to cancel their current contract, you need to train them, and then it takes at least 6 months to get to that goal.

So in summary, first ask people, what is possible. Combine all the events your team has given you, model it into one process, present your plans to the team and if your team agrees, you can eventually go to an investor to collect money to pay for it.

How specific are the day to day goals?

We started out with creating different sales teams for different markets. Then we ask those teams, with the resources and people you have, what do you think would be possible with regards to montly reurring revenue? And how do you plan to reach that amount?

Then again, we think about, if we want to get to this amount of revenue, we need to run this many pilots, we need to give this many demos and we need to have this many conversations. Then, to have this many conversations, I need to open this many doors and the market is this big, so there are this amount of targets I can find, so every week we need to write to this amount of people.

Now we’re measuring every week, are you sending enough emails, enough LinkedIn messages, did you get enough meetings, did you get to give the right amount of demos, are we running enough pilots. If not, what’s going on?

Qualitatively, they need to publish content, so what’s the content they’re going to publish this quarter, which fairs are they going to attend this quarter, what’s the budget they need for these fairs.

All these goals are quite detailed, because if you’re not getting to your scheduled MRR, you can closely look at what went wrong. If you’re not measuring, you can’t find out what’s happening and this can go on and on for months or years.

What are signs that you should increase efforts in a certain market?

I want to start out with a warning. Even though you can have interesting meetings with customers, a market might still not work out. Competitors might continuously discuss how interesting a market is, without showing actual revenue. Which will make you believe it would be great for society if the problem you’re working on would be solved. However, no one’s willing to pay for it.

And in the end, that’s the only thing that counts.

When do you stop a certain project or abandon a certain direction?

Every month, you set revenue goals, so every month, you can see if you’ve reached your goals. To see if certain revenue is scalable, you make the distinction between strategic and non-strategic revenue. Is one customer aligned with your roadmap or are we building a lot of features for this specific organization? If the second case, it’s difficult to scale, so you have to discontinue that approach.

Do you set goals to improve your goal setting?

Basically, what we do is every week we divide tasks, based on opportunities. But of course, going after one opportunity, means you can’t go after the other, so these are discussions that are held on a co-founder level.

We also understand that it takes a year or two to understand a market, before you’ve validated the proposition. Which emphasizes the importance of execution over the discussion. You need to talk to people, you need to try and sell your service and then basically, based on sales results, you find out if there’s a market.

Do you treat goals in your private life the same way as you do with your professional goals?

When I got my university degree, I thought, if I have to work for 40 years and it takes 5 years to realize if a certain environment fits, I have 8 tries. So, starting a company and building my own work environment didn’t feel like such a risk.

Plus, I really enjoy the freedom and being able to build something that is close to me and would stimulate me. So I organized my life to be able to live without a lot of money at first, which worked out really well.

I have to say that a few years ago, we raised a couple of million in equity funding, and it does feel nice to have enough money in the bank to realize things will be fine for a while.

What were your personal goals when you started the company?

Most importantly is that we wanted to create an environment where people, including ourselves, wanted to work. A lot of people experience a lot of pressure in their jobs, look at the increasing number of burnouts. We wanted to build a sustainable, long-term focused environment, a relaxed environment, through treating people well and coaching them. This eventually also lets us beat our competitors.

We believe it’s very old-fashioned to look at your team as an asset that you need to get the most out of. Here, we combine having fun and adding something valuable to society.

This also translates to who we work with, and therefore, what customers we even say no to. Prospects should not have to be completely green, but they need to add something to society as well. The projects you work on attract the kind of people you need to hire, so if you’re not attached to your customers, you will not feel attached to your team.

How did you set early stage goals?

We started in a room with nothing but whiteboards. We started sketching while we didn’t know which markets to approach.

In the beginning we needed to test various markets, so we needed to get as many prospect meetings to figure out which market was the most interesting one.

We got out of bad markets and into a strong one by iteratively learning from prospects, going through sales cycles, giving demos and running pilots. By taking on a lot of projects, we learned the workforce automation market was the most appealing.

How did you transfer your goal setting to your first hires?

First of all, some of our current best employees actually contacted us in the beginning. They are the ones we now rely on, our second line in command, so to say.

They were attracted to us because we were doing things differently technologically and as a startup, we tended to attract people who prefered a fast-paced environment and who wanted to directly collaborate with the executive team. As opposed to having several managers in between when you’re at a big firm.

I always suggest recent graduates to work at a startup, because the learning curve is incredibly steep. As long as you work with people you can actually learn from.

When it comes to goal setting, it’s important to realize that we were all in the same room at first and it’s way easier to monitor your team, because you are part of the same team. You do the same work. It takes less quantifiable goals, because you will notice directly when someone performs or doesn’t.

Next, it’s important to make early hires part of the success and failures. Even when you work with remote teams, like we did with a team in Ukraine, you have to make sure they feel as part of the organization. For example, by placing one remote team member in one team and another in second team. You don’t want anyone to feel as a project team that gets cut off when they’re done. Or get them confused when you deviate from your big goal. Because that will eventually lead to you to lose support from your team.

How does goal setting engage team members?

In the end, you can have the best goals, but if you don’t communicate them, they have no value. So you need to show your team where you are, where you want to be, and guide everybody in the right direction. Goal setting supports that process.

Having clear and measurable individual goals also makes it transparant what you expect from your team members. Which not only reduces stress, but also makes it easier to say goodbye when a hire is not a right fit.