3 Hard Conversations Worth Having

Difficult situations are never fun. Unfortunately, as product leaders, we encounter them often. More unfortunately, ignoring them usually isn’t going to make them go away. Having an honest conversation is the first step. Here are three such conversations that are worth getting out of your comfort zone for.

My 9-year-old daughter recently discovered a super fun and funny app. It’s called kids police. Do you know how some parents tell their children that a police officer will come if they don’t finish their dinner? So someone created an app where you can choose the situation (they don’t want to go to bed, they don’t want to get into the shower, etc.), and then you “call” the police. A recording on the other side plays, with only the police officer’s part of the conversation. So you “call” the police, an officer “answers” and says ‘yes, what’s the problem?’. Then you can say ‘my daughter doesn’t want to go to bed’ and the officer “answers” ‘what? Why?’. You explain what’s going on, they say it’s unacceptable and that the kid must go to bed or they will come, etc.

In our family, we use it as a joke. My daughter calls the kids’ police when I limit her screen time, or occasionally when I don’t want to go to school. It’s a fun game when used this way. But I’m guessing that there are parents who actually use this app to show their kids that the police will truly come if they don’t finish their homework. 

Whenever we play with this app, I keep telling my daughters that I will never use it – or any other such means – to trick them. No matter how hard it is going to be, I am going to face the situation honestly. I know parents who tell their kids that they ran out of chocolate just because they don’t allow the kids to have any more, and want to avoid the hard conversation. I can understand why it makes sense – after all, if there is no chocolate left, there is no point in discussing it anymore. But I, personally, expect myself to deal with the truth even when it’s unpleasant and work with what I’ve got.

At work, tricking your peers is not really an option, but often we still don’t want to face the unpleasant reality and avoid having these much-needed hard conversations. Some situations might be naturally resolved over time, even if you do nothing. But most of the time these challenges won’t go away unless you take action to resolve them. These hard conversations are a necessary and great start.

How can you tell if what you are facing is going to go away naturally or not? Here are three situations that surely require your action. Start with them.

When Strategy Doesn’t Meet Reality

It is common for product leaders to assume the company strategy is a given and they are operating within its well-defined limits. I personally see it differently and believe that shaping the company strategy is an important part of the product leader’s role (you can ask the CPO Bootcamp alumni – I can’t stop talking about this point). But even if you disagree and feel you can’t change the strategy, often times when you come to implement it or break it down into a product strategy, you find gaps and contradictions. It is only in the process of doing the actual work, that you can find what was overlooked during the strategy phase. Some of these gaps are easily addressed, but others require a change not in your plan but rather in the strategy itself. 

For example, sometimes a company strategy is aimed at entering a specific market segment (let’s say you started with SMBs and now want to get into enterprises). Once you start working on the product strategy which includes a deep dive into the personas at such enterprises and their needs, you realize that ‘enterprise’ is too wide as a definition, and there are a few sub-segments within it. Each such sub-segment might require a different product or at least a different prioritization of the features you will have eventually. So how do you continue from here? 

The only answer is to speak up. Go back to management and open the discussion, even if it’s not an easy one to have. 

The CEO may not like hearing that their strategy is still lacking – putting ego aside, it means that what they thought was closed now needs to be reopened, and it feels like going backward. In a company that needs to move fast (which means any company these days) and with so many other things on the CEO’s plate, it’s easy to understand why this conversation is not going to go smoothly. 

But the alternative of having such a conversation is much worse: not only do you need to decide on your own where to take it from here but also other important stakeholders won’t be aligned on the specific direction you have chosen. This means that marketing, sales, and customer success for example won’t be able to play their part according to the specific direction you were leading to, and it will be very hard to achieve an overall product success this way.

One way to make this conversation easier though, is to come prepared with a solution that everyone around the table can agree to. It means that you need to consider everyone’s point of view, think about their objectives and objections, come up with a number of alternatives, and help everyone have a productive discussion.

By the way, don’t expect anyone to thank you for bringing it up and getting it resolved. Unfortunately, this is simply considered doing your job. But eventually, when everyone is aligned and the product goes in the right direction, you will know you did the right thing. 

When a Disagreement Becomes a Deadlock

How many times have you argued with someone you couldn’t convince? It happens often, and it can be frustrating. Even more challenging is when you can’t move forward without the other person’s consent – a very common situation for product leaders. 

So if you have tried everything and nothing worked, how do you continue from here? You might be tempted to continue on your own and ignore the conflict here, but it usually won’t work. If you sigh every time you think about it, it’s a good indication that you need to have an additional conversation.

Since you already had many conversations that didn’t lead to a resolution, this time you want to approach it differently. You want to carefully untangle the disagreement and get to the root of what it is that you truly see differently.

If the discussion doesn’t lead there naturally, you can take the opposite approach: establish common ground by talking about the things that you do agree on. Even though it might feel as if you didn’t agree on anything, it’s usually not the case. When you start stating what you do agree on, you do a few things to promote the discussion. You show the other person that you are truly interested in resolving this rather than ignoring it or forcing your own opinion. You also show that there are things that you agree on, so it frames the disagreement as much more manageable. And you help everyone think it through once again and organize their own thoughts in the process. 

At this point, you will probably discover that you agree on most issues and that the disagreement is centered around one topic. After doing this, even if it’s a big issue, your conflict becomes much more specific and smaller than what both sides previously felt. Identifying the exact differences makes sorting them out much easier and the next step in the resolution is usually straightforward. 

For example, if your conflict comes down to whether or not you believe your current customers experience a certain issue, it’s something relatively easy to figure out. Go interview a few, dig in your existing records (calls, feature requests, interviews, email threads with them, etc.) to find an answer, run a survey, and I’m sure there are other means you can think of. Note that this next step is still part of the conflict resolution. Once you have the answers go back to the discussion table to analyze the information and agree on how to take it from here.

When Something Doesn’t Work

You know when it happens. You probably have been going around for weeks with this annoying feeling that you wish things were different. Unfortunately, anything you try doesn’t make it go away. That’s when it’s time to admit that it just doesn’t work.

It can be an employee that is no longer able to deliver on what you really need from them, no matter how hard you tried to work with them on their growth. It can be a feature or even a whole product that you tried to get people to use, and no matter what you tried, it didn’t move the needle significantly. Sometimes it’s an entire strategic direction, for example, if your market has changed and you see that you are left behind.

Admitting these even to yourself is never easy. It feels like a failure, and it usually has unpleasant consequences that you are afraid to even think of. Do I really want to start hiring and training a new employee in today’s market? Can I kill the feature despite the fact that some users are using it consistently? What should I even do if my market no longer works? It’s too scary to even consider.

But these situations, too, won’t go away just because it’s hard to raise them onto the surface. The opposite is true: the more you are willing to talk about it, the higher are the chances that you will analyze it well and find a resolution.

Remember that admitting to the failure and saying it out loud for the first time is the scariest part – but once you do it and see that the world did not crash, you will be able to think about it and deal with it rationally and not emotionally. For example, if you tell your manager that you are considering getting a certain employee fired, they will most likely ask why and help you think it through. If your gut feeling was right, you will probably be able to provide them with good, rational reasons, and come up with an action plan. 

* * *

When I tell my kids that while we still have more chocolate left, but still they can’t get any, it can be unpleasant momentarily. But the long-term gain is immense: they learn about healthy nutrition, they get to practice living within certain boundaries and dealing effectively with frustration, and most importantly they learn that they can trust me to always tell them the truth, even when it’s hard, and will probably do the same when they face a harsh situation.

The long-term gains of having hard conversations at work are different, but still very significant. Don’t sacrifice them just because they are hard. I trust you to do the right thing!

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

Share this post

Never Miss a Blog Post

Subscribe to my newsletter to get new blog posts to your inbox, and unlock unique special offers

Registration for the 11th

CPO Bootcamp

in now open!

Registration for the 11th

CPO Bootcamp

is now open!

A special earlybirds discount:

10% off

the early registration price,

until April 13th.