The Fine Line Between Aggressive Goals and Complete Fantasy

Setting goals is hard. You always need to balance between what you really (really) want, or even need, and what reality can support. And being super ambitious isn’t always the answer. Here is a fresh approach to setting goals that will keep you rooted both in reality and in vision.

As I recently wrote here, I’m a hard worker, and always have been. Even as a child, I wanted to do so many things, and get to the top at each. In my fifth and sixth grade, I was a professional swimmer (as professional as it gets at these ages, two hours of swim practice six times a week, and that’s before the additional gym workouts and the full-day competitions on weekends), a pianist (two practices a week at the local conservatory, theory lessons on another day, and practicing at home every day), attended a gifted kids after-school program, and of course girl scouts. These days I’m exhausted just by writing this, but back then it didn’t feel like too much. I absolutely loved it.

Towards the end of my sixth grade though, my piano teacher wasn’t happy. She said that I have too much on my plate and that I needed to quit some of these activities. She meant, of course, that I needed to make more time for my piano lessons, and especially for practicing at home, but that wasn’t what I chose to do. Instead, I quit piano, after having played for six years.

Don’t get me wrong, I don’t think that had she advised me differently I would have become a professional pianist growing up, but I do think that setting goals that cannot live in reality (because I wasn’t willing to quit any of the other activities) can do more harm than good.

The obvious reason is that if you push too hard your people might give up altogether, thinking that you are asking them to do the impossible, but in running a business there are far more important reasons to carefully look at the goals you set.

Here is what you can do to make sure your goals are solid, without compromising your ambition. Note that I’m talking here about business goals since that’s where most impact is, but the same guidelines apply to any other type of goal, even personal ones.

Goals That You Need but Can’t Get To

If getting to your goal feels like a walk in the park, you probably weren’t ambitious enough. As company leaders, management always wants to take the company to the highest possible achievement at any point in time, so your goals should always feel nearly impossible to meet. As a result, we all got used to setting goals that seem impossible while trying really hard to get there still.

However, setting the goal is just the beginning, and if you truly need to meet the goals on a strict timeline, you better understand how you are going to achieve them. The difference between a nearly impossible goal and a truly impossible one can make or break a company.

Here is an example that I see with many companies: it often happens toward an upcoming funding round. Thinking backward from funding or valuation goals, you calculate where you need to be financially to be able to raise a great round. Then, you pair it with the length of your runway, and you see that you need to be there within a few months. Realizing where you need to be is an important first step, but to make it a reality you need to plan and see how you get there. You actually start doing that, but you don’t complete it. You couldn’t get to a reasonable plan quickly (because there isn’t one?), and since time is of the essence here the CEO usually simply sets the goal and encourages everyone to work as hard as they can to achieve it. 

If this is a company I work with, I always ask the founders if they think it’s achievable. Understanding their financial situation, it’s a question that is very hard to answer realistically, because they simply can’t say no. The consequences of not being able to meet this goal are so severe, that they can’t even think about having to deal with them. Note that startup founders are used to making the impossible happen, as they are creating a whole new world for all of us. So when I ask this question, they might be puzzled for a moment, but then usually say with conviction that yes, it can be done!

Honestly, they can’t say anything else even to themselves. But the problem is that if it can’t be done, at this point you are doomed, because when you realize that you are not going to meet that goal that you must meet, it is going to be too late to do anything about it.

Create a Real Plan

The best way to know if a very ambitious goal is still achievable or not is to simply plan and see how you are going to meet it. It’s not easy by definition, because the goal is ambitious, but you shouldn’t give up. If you are serious about meeting the goal, you better know how you are going to do it. To remove the constant struggle between where you want to be and where you can be, forget about the goal for a minute and build the best plan you can – this time bottom-up.

You need to understand where you are at today, how likely it is to continue at the same pace (good or bad), what you can do to expand or scale and where it is going to get you at the end. If it is almost near where you need to be, and some additional push will do the trick, you are good to go. But if it’s not getting there, or alternatively if your goal is so strict that you cannot allow yourself to miss it even by a little, if you can’t see how you get there, at some point it’s time to say that you are not going to make it, and think about an alternative.

Sometimes Plan B Is Actually the Better One

This is especially true if your plan A is not doable, even on paper. In that case, you better realize early on that something needs to change, either something fundamental about your approach (e.g. sales-led vs. product-led growth), the market(s) you operate in (is it time to focus or actually open other fronts sooner than you intended to?), or the goal itself. Can you live with a smaller, more achievable goal? Where does it take you? These questions are not fun to deal with, because deep down inside you still hope you can get to the goal you really needed. But if you want to do yourself and the company a good service, put that hope aside for now. You can always add it back later on.

Force yourself (and the management team) to deal with these hard questions upfront. From my experience, there is almost always an additional option. You might find yourself with a good plan that gives you almost all of the value you need but with lower risk, or can even get you to better places. 

To get there, you need to understand what you are really after in the goals you set. For example, if you want to show traction with a new business direction, ask yourself what would be a good enough outcome to show that traction. What the MVP of the goal is, not the best possible one. It might be, for example, that the desired outcome to show traction is 20 new paying customers by the end of the year. But since we are already in Q4, and you currently have one customer, that’s not really realistic. On the other hand, this goal of 20 paying customers might be the full realization of what you really want to show – traction to the new business direction, which means it includes a lot of cream and cherry on top. Can you remove the cream? What does it really mean to show traction to investors as you start talking to them? Perhaps, if you have five customers who are paying and using your product daily by the end of the year, then that’s a great start. Investors won’t put money before they see that you can grow beyond five, but they will anyway not put money on day one that you talk to them (although in today’s market you can never know 😉 ). 

Which do you think is a better goal? 20 paying customers (whether they use the product or not) or 5 paying very happy customers? Which one shows better traction? I would say it’s the latter. So sometimes by forcing yourself to cut where it hurts, you actually get a better outcome.

I’ve seen this recently with the CPO Bootcamp. Due to the demand, I wanted to see if I can add another batch sooner than I thought. To do that, and taking into consideration the April holidays that I didn’t want to interfere with the program, I decided to see if I can make the program slightly shorter. Trust me, that’s not an easy decision for me to make! Attempting to address all of the challenges of the product leader, the program is so busy as is, so making it shorter felt like a compromise I didn’t want to make. But I put the hope that I can find a solution without it aside and forced myself to think about it seriously, knowing that I can always go back to the original program if I wasn’t happy with the result. So if I wanted to make the program shorter without compromising its quality, what would I do? Thinking about it this way, I suddenly realized that the solution was there in front of me all the time: there was a single consistent request from all batches up until now, to add another face to face workshop in the middle of the program, and suddenly it made a lot of sense! I added another workshop instead of 2 lectures, which allowed me to also deal with other places that I felt could benefit from the work you can do in a workshop vs. in a zoom session. The solution I found absolutely upgraded the program, and so I was able to meet both my goals. Not only did it no longer feel like a compromise on quality, it was actually a much better plan that I’m super happy with. But I couldn’t have gotten to this better plan B if I didn’t let go of plan A.

Where are you sticking to goals that you really need to meet, but can’t? Let go of them for a while and think about it from scratch. The outcome might surprise you.

Our free e-book “Speed-Up the Journey to Product-Market Fit” — an executive’s guide to strategic product management is waiting for you

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