When I first moved out of R&D towards my product management career, I reported to a manager who was known to be very demanding of his people. I knew it before I joined him in the journey to launch and make a new product a great success, but since ‘challenge’ is my middle name I was sure that it will be fine. It was a small team of just me and him. We were working with sales, on one hand, to help them sell and find product-market fit, and with R&D on the other hand to help them develop the right product. It wasn’t even called product management back then but in essence, it was just that. I was surprised by how much I loved my job. I always thought I belong in R&D and was only stepping out for a short period of time, just to come back more knowledgeable. But as you know this never happened, I fell in love with this new world and have never left it since. 

My boss and I worked well together. I learned so much from him, and it felt like an A-team on a mission. It was exciting. However, at some point, something started bothering me. I didn’t really know what it was, I only knew that when I got emails from him I wasn’t as happy as before. I took some time to see if it was going to pass without any action on my side, but when it didn’t I realized I have to do something about it. The problem was that I only knew that I felt bad, but I didn’t know why, and so there was nothing I could do about it.

Luckily, this was shortly after I learned coaching, and so I had the tools to better understand what’s going on. I was also brave enough to look into what was truly there, even if it wasn’t going to be pretty. It was exactly that barrier that prevented me from understanding what’s going on, and when I was willing to truly look inside and face whatever it is that I will meet, I knew the answer. The problem was that I didn’t want to work as hard as I thought my boss wanted me to. For me, this was a big deal. I was always a hard worker, and having any amount of work being too much was simply not something I ever allowed myself to feel, accept, or say out loud. I was still working very hard, but getting tons of emails over the weekend got me beyond my limits.

When I realized that this was the root cause of my bad feeling, on one hand, it was easier because I now knew what’s going on, but on the other hand, left me still with the problem of how to tell my boss that I don’t want to work as hard as he needs or expects me to do.

I needed to do some work with myself first. I asked myself what I really wanted. I can assure you it wasn’t being at the beach all day, or working in any form that would be considered lazy or even relaxed. I loved the excitement of the quick pace, and I didn’t want to give it up. I just didn’t want it to be there 100% of the time, and specifically on weekends. I truly needed that time to rest so that I have the energy to work full speed the following week. 

Now that I knew what I wanted, I could talk to my manager. I asked for a 1:1 and said that I had a problem with how we worked recently since I felt that he wants me to work harder than I wanted to. I deliberately didn’t say harder than I could, since that wasn’t the truth. I could work harder, but that wasn’t what I wanted. I gave the specific example of getting his emails in the middle of the night and over weekends (this was back in 2006 when we were still able to disconnect over weekends. Different times). You can imagine his surprise. I was ready for a long speech about how important it is to work at this pace, but I heard something completely different. I heard that he is very happy with my work and that the fact that he is a workaholic shouldn’t impact me. He asked that I would treat his late night and weekend emails as if I got them in the following working day. He didn’t say he would stop working this way, because that’s what worked for him, but I could accept his request and treat these emails the way he wanted me to and not the way I assumed he wanted me to treat them. This worked for both of us, and I kept learning from him a lot about the business world, how to work with customers, some sales work, and many other things. Raviv passed away a long time ago, but to this day I feel grateful for everything I got by working so closely with him.

This single conversation re-established the trust between us, by making sure that we are in full alignment. As with any relationship, when there are hidden issues that are not communicated, it’s very difficult to even work together effectively over time, let alone trust each other. Grudge and trust can’t live together under the same roof.

Here are a few simple steps that you can take to ensure that you treat the problems at the root cause, and have brave and meaningful conversations with anyone you work with.

Understand What You Feel

In order to solve any problem, you need to first acknowledge its existence. When it comes to relationships, it is not always trivial. As product leaders we are so entrenched in our job, we give it everything we can, that saying – even to yourself – that something doesn’t work for you can be troubling. The thing is, that if something doesn’t work for you, it doesn’t work for you, and ignoring it – in your actions but also in your thoughts – isn’t going to make it go away. It will continue to not work for you still. 

If you are committed to getting it resolved, acknowledging that the problem exists isn’t going to make things worse. It’s just a step in the right direction for getting it resolved.

It often feels like this: you are in a meeting, someone says something, and you feel like you were punched in your belly. Something just doesn’t feel right. Depending on your style and level of confidence, as well as who said this comment that made you feel bad, you might stop right there and clarify it, but many times this isn’t the case. I know that at least for me, it takes longer to fully understand why I feel bad and what is it that I want to say. Honestly, many times my immediate reaction to myself is that I shouldn’t be so sensitive and shouldn’t make a big deal out of it, that ignoring it would be the best option.

But ignoring something when it still bothers you inside is not going to help you. So even if it’s a few days later, if you still feel bad about it, be brave enough to look into it. Ask yourself what is it that bothers you exactly. What subtext did you read in what the other person said that you disagree with or are threatened by? Trust me, clarifying this to yourself – even without doing anything – will make you feel better.

Understand What You Want

Once you understand that there is a problem, and you clarified to yourself what it is, you need to ask yourself what is it that you want. It’s not always a simple or straightforward answer, as it was in my case above. I didn’t want to set tight boundaries around my working hours because I still wanted to go all in about it. What I wanted was more refined, and wasn’t solely at the tangible outcomes. How many times do we just want to hear that we are doing good work? 

I remember that when I was a product lead at Imperva I once complained to the CMO that everyone was questioning me all the time. It was really hard (I’m sure you can relate). His response was simple: he said he is sure that I know my product and market better than anyone else in the company, and that he trusts me. This did wonder for me, although nothing changed in reality: people kept challenging me all the time, but I no longer felt that this was a problem. It now became simply part of the dynamics, and it was fine.

Clarify to yourself what would solve the problem best for you, and be honest with yourself. There are probably many options that would satisfy you, so understand what they are and distinguish the must-haves from the nice-to-haves. That would help you come prepared for the next step – having the actual conversation.

Talk About It

To change things in the real world you need to take action in the real world. That’s how it works. So now that you have acknowledged the problem, and you know what you want, it’s time to talk about it with the other person you had the issue with. 

As in my case above, come prepared for negotiation, or better yet – for creating a solution that works for everyone, together. Lay your problem as the starting point of the conversation, not as the conclusion. From my experience, in many cases, those incidents bother the other person as well, perhaps not for the same reasons, but nobody likes working in disagreement.

The structure of the conversation should be something like that: First, you give context and say that there is something that bothers you. Then, describe the event that you refer to. Next, explain what bothered you. If you are referring to subtexts, say that this is what you felt, and don’t treat it as if it was the objective truth. Then ask the other person how they experienced this event. Give them an opportunity to share their point of view, from a non-defensive place. To encourage that you can say that you assume this wasn’t pleasant for them too, and that you’d like to hear their perspective.

Only then, once bad blood is cleared, you can start discussing solutions together. You can suggest what you thought of, and ask them what they think. In some cases, it makes sense to update your suggestion based on what you heard in the first part of the conversation. Either way, make sure you are left with something you are both happy with. You’ll be surprised by how much these conversations not only resolve the issue at hand but also establish a much closer relationship between you and the other person. 

You might ask yourself how this is related to trust, as this is what this article series is about (see part 1 here). Well, once you establish that you can resolve even the most sensitive issues between the two of you, you can feel much safer walking side by side on your amazing journey together, knowing that you can overcome any bump in the road. And that’s what trust is all about, isn’t it?