How to approach tough conversations

How to approach tough conversations

We’ve all had tough conversations: Give negative feedback to a colleague, suggest a radical idea to our boss, or stand up against something wrong publicly.

These conversations are uncomfortable, because they have the potential to create conflict. In the worst case scenario, people will yell at us, react violently, or have us fired. So sometimes, not sharing our thoughts is the safer option.

No. Wrong. That’s not an option. Not at a startup.

In my opinion, not exposing what’s on our mind translates into not believing in our team’s ability to discuss bold ideas and receive critical feedback. As result, we stop seeing different perspectives and limit our ability to innovate. If we’re withholding a thought because we fear conflict, we might as well quit. It’s a sign that the workplace has a close-minded culture. Why would we waste our time at a startup where we cannot be honest with each other?

If we’re withholding a thought because we fear conflict, we might as well quit.

As leaders, it’s our duty to create a safe environment where team members can hold tough conversations with each other. Teams need to be able to disagree, to share constructive feedback, and to be honest without getting emotional.

To make tough conversations less uncomfortable, we need to focus on the issue rather the individual. The idea rather than the person behind the idea.

To this effect, allow me to share a three step approach that helps me approach tough conversations:

  1. Communicate the context of the conversation, along with supporting facts to our argument: Sharing why I’m talking ensures that the other party understands the context of the conversation. Next, I expose non-arguable facts and stats, which the other party cannot disagree with. The goal at this stage is to start from the same page.
  2. Reveal how we perceive or interpret the facts listed previously: I now reveal my opinion of the situation by sharing how I feel about the facts or stats exposed. To avoid debate, I state clearly that this is my personal opinion, and that I simply want the other party to acknowledge my perspective, not necessarily adopt it.
  3. Get onto the same page about the problem, and come to an agreement on how to resolve it: Finally, I open the conversation to the other party to see how they feel about the situation, and try to get onto the same page again by seeking their perspective. In other words, I’m validating my interpretations and assumptions. If I have an action item or takeaway for the other individual in mind, this is where I work with the other party to agree on it.

Let’s explore how to use this framework in real-life scenarios.

I. Giving constructive feedback to a colleague

One of the most common and uncomfortable situations we encounter at work is the urge to give feedback to a colleague. Maybe our colleague made a mistake, did something that we would never do, or even offended someone.

To avoid conflict, we have a tendency to not share our feedback. Yet it doesn’t have to be uncomfortable! Let’s think about the situation in a different light: The reason we want to share feedback is because we want the other individual to do better, to be more effective, or to learn something new. Guess what: They want the same thing!

So here’s how we apply our three step framework to help our colleagues grow:

  1. Describe the context and facts that support our argument: Hey, can I chat with you about increasing our team’s ratio of follow up sales calls? I noticed that you’re emailing prospects to schedule follow up calls.
  2. Reveal how we perceive or interpret the facts listed previously: In my personal experience, prospects take a long time to get back to me by email, if at all, so I simply schedule the follow up call while I still have the prospect on the phone.
  3. Get onto the same page about the problem: Do you have problems getting follow up calls scheduled via email as well? Have you tried scheduling it right on the call?

Let’s explore another case:

  1. Describe the context and facts that support our argument: I’d like to discuss how to make our meetings more productive. In the engineering review we just had, you raised your voice at John when opposing his idea on X. Here’s a recording of the conversation…
  2. Reveal how we perceive or interpret the facts listed previously: In my opinion, that was disrespectful to John and unprofessional. Even if you disagree with his idea, there is no need to raise your voice and intimidate him that way. It made everyone in the meeting, including myself, very uncomfortable.
  3. Get onto the same page about the problem: Do you recognize that it was disrespectful and unprofessional to raise your voice to someone? What do you think is a solution to this?

In the scenario above where the fact or event that we’re leveraging to illustrate our point is very specific, I recommend bringing it up as soon after the event occurred as possible (especially since we usually don’t have voice recordings of meetings). This avoids scenarios where the other party cannot remember details of the event. Often times, people are unaware of their bad habits.

II. Saying no to an idea

Rejecting someone can be difficult. It can destroy a person’s confidence, and cause the person to never bring up an idea again. So let’s explore how to say no with reason:

  1. Describe the context and facts that support our argument: I’d like to chat about how to best use our team’s resources and making sure we’re setup for success. First of all, thank you for bringing up the idea of hiring a consultant to help coach the sales team. Fact is, our current budget doesn’t allow us to hire such a consultant. Our budget is currently fully allocated toward salary, bonuses, sales software, and advertisements. It thus leaves no room for a consultant.
  2. Reveal how we perceive or interpret the facts listed previously: In my opinion, the team can improve their sales skills individually by reading about the Sandler system online and save money that way.
  3. Get onto the same page about the problem: Do you agree? What do you think?

Note how we didn’t give an absolute no. Instead, we explained why it is not possible to pursue a certain idea. We left the door open to explore alternatives and for the person to debate our opinion. It’s as desired to keep the door open to radical ideas.

Who knows… perhaps the team may choose to forfeit their bonus to get a sales coach instead. That’s fine by me. Or maybe I’m not aware of evidence showing that a sales coach has a higher ROI than ads, in which case it’s more logical to hire the sales coach and reduce our ads spend. Often times, explaining why we’re saying no will catalyze disruptive and innovative ideas. The one thing to avoid doing is saying no without reason – it communicates that we’re either close minded or don’t trust team members with our reasons.

III. Disagree on a decision with our boss

It can be most intimidating to disagree with our boss. That’s because we may create a conflict that we are unlikely to win. However, we don’t have to make it personal, and we can use the opportunity to try and understand whether there are other factors in a decision that we are not exposed to. So let’s give our boss the benefit of the doubt as they may have additional intel:

  1. Describe our expectation and facts that support our argument: Boss, I’d like to discuss how to best position our product for success in the upcoming quarter. Specifically, the decision that was made around building feature 1 rather than feature 2. Fact is, 60% of customers surveyed want feature 2 compared to 45% for feature 1. Feature 2 is also estimated to take half the time to complete relative to feature 1. Finally, the estimated yearly ROI of launching feature Y is 50% higher than that of feature 1.
  2. Reveal how we perceive or interpret the facts listed previously: In my opinion, to increase our revenue and achieve our growth targets, it is most beneficial to the company if we prioritized feature 2 instead of feature 1.
  3. Get onto the same page about the problem: Do you agree? Are there other stats or factors that I’m not aware of that led you to decide to focus on feature 1 instead?

This approach gives our boss a chance to be transparent and share why they think developing feature Y is more important, and for us to learn more about our boss.

Before I end this blog post, allow me to share a good HBR article on how to approach tough conversations, check it out here: https://hbr.org/2015/01/how-to-handle-difficult-conversations-at-work


Recommended exercise

Let’s pick something that we’ve struggled to communicate to someone (boy are there many of those…) and practice communicating it with a trusted friend or colleague.


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(Featured Photo © Jeff A. Goldberg)

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