< More blog posts

Doing hard things: why is it so hard to do well?

April 15, 2019

The irony is real.

Ask any Product Manager what the least favorite component of their job is, and I’d be willing to bet the majority of responses correlate with something in the realm of “having hard conversations”.

  • They can be incredibly uncomfortable.
  • They’re not inherently easy to do.
  • If they’re not done well, they can lead to a lot of added complexity within your project, as well as within the relationships of the team and client.

Pretty exciting, yeah?

woman cringing at awards ceremony gif
yep.

I really hate to break it to you, but as cringe-worthy as some of these conversations can be, they’re not going anywhere any time soon.

Let’s take a collective deep breath, and walk through some of the ways we can make these better, together.

We got this!

Hard Conversations: What Actually Makes Them Hard?

Having a conversation typically isn’t seen a strenuous activity (excluding the idea that communication in its general nature is difficult), so what exactly shifts a conversation from something that’s effortless to something that’s grueling?

What if it’s you[r emotions]?

That’s honestly okay, because it probably means that you care. Having an emotional connection to your day-to-day work means that you’ve got passion for what you do, and that you’re likely concerned with doing your job well. But it can also mean that you’ve got challenges to overcome when the honeymoon phase is over.

I like to think of this as healthy stress — motivation to do well for the projects/teams that you care deeply about. Embrace and respect the passion you have for your project, but don’t allow it to overcome you. Use it to your advantage.

What if it’s you[r mistake]?

Jim from the office making face at camera
oops.

As unfortunate as it is, we all are guilty of imperfection and we all screw up. Sometimes it’s a completely siloed mistake, and sometimes it’s a mistake that the team has made together. The goal with any mistake, though, is gaining the courage to own up to it and grow from it.

There’s a lot to be said for those who own what they’ve done, and even more to be said for those who choose to make changes moving forward. Do your best not to let the anxiety feel too heavy, because (in the words of the esteemed Hannah Montana): everyone makes mistakes, everyone has those days.

Hard Conversations: How Can We Make Them Less Hard?


Ask questions, and ask them often.

If there’s one thing that I’ve learned that applies to all areas of life, it’s that asking questions (particularly the ones that aren’t so easy to ask) is the best way to gather clarity. Hard conversations can be softened by asking targeted questions, aimed to provide clarity or alleviate miscommunications.

Seeking and asking for clarity should always stay top of mind when you’re diving into difficult conversations. If you ever find yourself having doubts about the intention or meaning behind why or what something means, simply ask for clarity. You’ll likely save yourself (and others) from additional or unnecessary duress when miscommunication occurs.

Talk through your thoughts with other people.

Discussing your plan of action with another co-worker or friend is a great way to get genuine feedback before you dive into hard conversations. There are a few key steps to ensure that this process works:

  1. Make sure the person you confide in is someone who is honest and trustworthy. You should feel comfortable receiving feedback from them.
  2. The feedback you receive should be taken into consideration and deeply analyzed. You will be the final decision-maker when it comes to the conversation you craft, so take any/all action items from this chat and thoroughly review them before incorporating or disregarding any of the components you received.
  3. Pay that person back in the future — lend your ear to that person in return.

Look inward before you look outward.

Remember when we talked about what actually makes conversations hard? Well, this is the time that we reflect on these components (and by components, I am absolutely referring to you).

  • Is the reason the conversation seems hard, because you feel sensitive to the topic, or personally impacted? Remember that the reason you may feel this way is because you legitimately care about what you’re doing. Acknowledge this, and find ways to press forward without overwhelming yourself.
  • Is the reason the conversation seems hard, because you/your team made a mistake? Remember that the goal of any mistake is two fold — ownership and growth. Determine how you found your error, and determine how you’re going to improve moving forward.

Hard conversations are just that: they’re hard. Making the choice to engage in a hard conversation is the first step (and sometimes the hardest). But by utilizing tools such as self-realization, seeking feedback, and ensuring clarity by asking questions, you will begin to shift perspectives and arm yourself with the confidence you need to succeed.

woman in front of american flag saluting with determined face
you got this, no doubt.