I recently led a product-market fit workshop at a known company in the Israeli tech industry. It is a well-established company, a leader in its domain, but it still needs to deliver new products to the market so product-market fit is a very relevant topic.

As we went through the workshop there was a point I wanted to make, that I didn’t have a slide for. To make the point I wanted to make, I shared a story from the time I met my husband. It turned out that they liked it more than the topic itself and now they want a workshop on romantic relationships 🙂

As you might have noticed from reading this blog, I share many stories related to my personal relationships as a means to talk about product leadership. Often it’s because so much of product leadership is about relationships. But the point I want to make today isn’t about relationships, and still, that’s what the story is about.

I met my husband when I was 29, so prior to meeting him I had a long time to experience and practice dating. While some of the dates ended with a clear ‘No’, either on my side, on the guy’s side, or both, other dates were ok and even nice. There were guys I dated for weeks or months, but then we realized it wasn’t working anymore. 

What was it that wasn’t working? It’s not like things have changed dramatically, or a specific event occurred that led to us breaking up. We had a good time and liked each other, but it wasn’t enough. At some point one of us realized that this isn’t going to be the relationship of our lives, so we might as well stop now.

This realization isn’t always easy though. It’s not that things are not working at all. If that was the case, the decision was easy. But when things are somewhat working, just not enough, how do you decide to end it and not drag it as is for much longer?

When it comes to romantic relationships, you can follow your heart, you can feel you want more, and since this is a once-in-a-lifetime opportunity, you can always ask yourself if this is the love of your life, and it forces you to choose one way or the other.

At work, things are much more complex.

The signals are always mixed, and with no clear incentive to come to a conclusion, it’s no wonder that the most common answer to product leadership questions is the professional equivalent of the romantic “It’s complicated”, namely “It depends”. 

The tool I want to give you today is to force yourself to turn the shades of grey into black and white.

Not because the reality is black and white, but because otherwise you can’t see clearly. The shades of grey are often too confusing and simply add noise when there is a clear picture in front of you if you just put them aside.

Here are four examples of the clarity you can get when you work this way.

Keeping an Objective Eye on the Market

Do people really need your product?

In an Israeli WhatsApp group for product leaders (In Hebrew) that I run, I recently asked (following the article about competition from two weeks ago) who is your #1 competition type. Some people mentioned “Do Nothing”. 

That’s a major red flag about the need for the product itself. Because if people are fine doing nothing about the problem you are solving, would they be willing to adopt a product and pay for it? Is the problem really that important to them?

The thing with that survey is that I only allowed one answer, and if forced people to choose. It calls for clarity and honesty. 

I then started talking to the people who marked this option, and suggested that they might see some traction because that’s how things are, but is it good enough?

If there is absolutely no one that likes your product, 0%, the answer is easy. If you see significant progress over time and are able to reach the results you want, that’s also an easy answer. But what happens when there are shades of grey? With hard work, you are able to sell your product, and also keep your customers on board. But is it enough? Are there many more like them? Will you be able to convert them? 

When you are in the trenches day in and day out, it’s sometimes hard to see the bigger picture clearly. But if I force you to a yes/no answer, you can’t lie to yourself. Note that it doesn’t mean that you have to kill the product, it might mean that you need to find a better use case where your product is really needed. You might decide to embark on the very hard journey of educating the market (relevant only if they do nothing because they don’t think a solution exists, not if they do nothing because they don’t care enough). But either way you will do it after making an informed decision, and not just by inertia.

Creating a Clear Segmentation

If I ask you to profile your customers, initially it would seem that each one is different. It might be true, but that doesn’t help us make any decisions or come to any conclusions. To be able to build a product that serves a clear audience we must define that audience clearly. And one of the best ways to do so is to see what worked for you so far.

I recently started working with a new client on product transformation. It’s a mature startup, with a number of products in the market, a leader in some categories and building up nicely in others. As is almost always the case, what seems to be execution gaps turn out to be product strategy gaps, and so we started with creating a clear product strategy.

At some point I gave the CEO homework: to analyze all the recent deals of one of the products and try to find patterns. I created a spreadsheet that they needed to fill, that included the customer size (it’s a B2B company), industry, and primary use case for buying the product.

At first glance, the results were a mix of three different use cases. But when we started analyzing them, we saw a very clear pattern: small companies had use case A, medium-sized companies went with use case B, and only large ones went with C.

The thing is that the analysis required turning shades of grey into black and white. For example, the large companies were mostly companies with 10K employees or more. There were, however, two deals with the large-company use case that were less than 10K employees. One was 9K and the other was 7K. What does that mean? Should we define the boundary lower than 10K? Does it mean that use case C is also relevant to medium-sized companies?

It is easy to give a complex answer, but if we want to create clarity and simplify, we must ignore the edge cases. We stated that only large companies had use case C. It allowed us to build for that use case with a clear audience and excel in it. 

And what happens if another 8K employee company comes in and has use case C? You can still sell them, but as in the previous example, you will know that it’s not a perfect match (perhaps on the pricing side of your enterprise agreement, it doesn’t have to be about the product) and can still decide whether you want to do it or not.

Identifying Bottlenecks

I write here a lot about the pirates’ metrics framework. I really like this framework as it outlines the human customer journey with your product and breaks it down into distinct categories. Whether your product is B2B or B2C, it’s people who buy it, and these people need to go through a certain journey to be able to say yes (and get others to agree if you are B2B). 

One of the ways in which I recommend using the framework is rating yourself in green-yellow-red for each category. It’s a simple exercise that you can do as soon as you understand what each category means, you don’t need to dive deep into how you measure each and you surely don’t need to actually measure anything. But you do need to choose. You can’t rate yourself on a 10-color scale. It should be clear and simple.

Once you rated yourself, it’s easy to see where your current bottlenecks are. Even if everything is green (which is usually not the case) and there is one yellow, it’s extremely simple to see where the problem is. In most cases, you’ll have many reds and yellows, and can still see where you need to focus.

If you still can’t see the pattern, try combining this with the segmentation from the previous section. You might find out that you have different colors for the same category when the audience is different. For example, you are great with activation for smaller companies, but not so great for larger ones. You might have great retention with women but not so much with men, etc.

Being Honest About Your Team’s Performance

This one is probably most similar to the relationship example that I shared at the beginning. At the Coach the Coaches session I attended with Marty Cagan he kept saying that as a product leader, you are as weak as your weakest team member. 

There are many things that can be done about that – from coaching to replacing them – but you can’t deal with it if you aren’t acknowledging that this is the situation. Generally speaking, people don’t like giving bad feedback, and they tend to drag things even though they don’t work well enough. I know I have done this in the past, and I learned the hard way that dragging this for too long has a significant price to everyone involved.

But again, to deal with such a situation, you must be extremely honest with yourself and acknowledge that what seems to work sometimes isn’t actually working. A minor progress, while it can give you hope, might also be misleading.

One way to turn shades of grey into black and white is to ask yourself if that person left would you be relieved or sorry? Two options, to force yourself to choose. 

If you take it to performance reviews (formal or not), I recommend a scale of 1 to 4, not 1 to 5. This way you must take sides, you can’t leave them with a decent 3, which is where most people would land eventually. You don’t need to change the formal scale of the company, but when you think about it for yourself, force yourself to choose. It might be hard, but it’s actually much easier than the alternative.