How to Prepare for a High-Stakes Conversation (and have a successful outcome)
Entering a high-stakes conversation can be daunting. You know what you want to discuss, but you’re unsure of how the other person will respond. Let’s delve into how you can prepare for a successful outcome.
First off, what makes a conversation high-stakes (as opposed to…a regular conversation)?
Typically there are two elements that make a conversation high-stakes:
You want something (and will be really disappointed if you don’t get it…like a budget for a project, a promotion, etc.)
You’re delivering bad news (like a project won’t hit the target and changes will need to be made)
PLUS…I find that these two things are coupled with one other factor: the relationship dynamic you have with the person you are speaking with.
Here are some examples of how the elements combine:
You want to discuss the future of your career and your aims for a promotion with a new manager (so the relationship is new and you don’t know how that person will react)
You need to deliver bad news to a stakeholder but you’ve just joined the company (so the relationship is again new and you’re unsure of the best way of delivering the message)
You need to give negative feedback to a team member but you have a really close relationship with this person and know that it’s going to be very disappointing with them (your close relationship dynamic makes it hard to separate your emotions from the message you need to deliver).
Step 1: What does a successful conversation look like to you?
Most people I speak with either have an idea of how they want to start delivering the message but aren’t sure of what the outcome should look like, or they are clear on what they want from the other person but they aren’t sure what success would mean for that person too.
Here are some questions to get some ideas flowing:
What message do you need to deliver?
How do you want that person to respond?
If you were in that person’s shoes, how would you want to hear the information?
What’s in it for them?
What do you want that person to do with the information after the meeting?
Step 2: How can you take a collaborative approach?
Usually, when we are thinking about a high-stakes conversation, we think from the perspective of “telling”. Sometimes, “telling” information can create a dynamic where the other person is set up to feel a need to respond defensively.
“This is what I want or what I know, what are you going to do about it?“
to…
“This is the information I have, how can we work together to move towards a positive outcome?”
This is good because it puts you both on the same level (or at least, in the positions you are in). No one is talking down to the other person.
Step 3: Make it about the topic, and not about the person
This step can be helpful depending on the situation. It’s another way of creating a feeling of collaboration because you are inviting the person to talk about a problem instead of implying that the person is the problem or is the cause of the problem.
Step 4: Does this message warrant 1 conversation or could it be split up into 2?
This question is more about your timeline - sometimes when we feel we are entering a high-stakes conversation, we feel that the answer needs to be reached within that meeting.
But does it?
If you knew you were going to have 2 conversations, then what would be the goal of the first, and what would be the goal of the second?
For example, let’s say you noticed that your team member isn’t performing well. Instead of committing yourself to one meeting where you tell them that their performance is bad, what if you committed to having two conversations where the goal of the first one was to investigate where they feel they are at right now and what challenges they potentially are facing? The insights you gain from that first conversation might help you better navigate and soften the next harder conversation about their performance.
Step 5: Who could help you with this?
By who, I mean two kinds of people:
A person who you think is a great communicator in general or a person who is good at communicating with the person of interest. What advice would they give you?
The second person is someone who you could role-play with (as a coach, for example, I often do role-play with people to help them verbalize what they want to say and refine their message).
Jason’s* high-stakes conversation story:
Let me share with you Jason’s story to illustrate the points above.
Jason, a senior consultant, came to a horrifying realization. The project he was hired to overtake would not be successful based on his analysis; the previous leader must have sold the company on a vision using baseless information.
He knew he’d have to confront the VP and thereafter the COO with this information. That the numbers don’t make sense and that they’d need to do damage control and reset their expectations.
Everyone in the company for the past 3 years had been working towards this vision and committed to a promise. He knew that his news would be letting everyone down.
When I first heard Jason’s story, I couldn’t find a core problem with how he would be delivering his message because while the topic sounded unfortunate, his idea for communication sounded clear. He had a clear understanding of how he needed to present the information to key stakeholders and that this was a reality they would all need to face.
So we dug deeper. What was really behind his concerns about communicating with the VP and COO?
“Well, I’ve only been working at the company for 30 days.” he shared. “I don’t really have relationships built with anyone and I don’t know how they’ll react.” he continued.
In business, there will be circumstances where you need to share information with people that will not be good news.
In Jason’s case, what made this feel like an even larger problem was that he feared that starting off his relationships with people in the company by sharing bad news would set a negative tone towards him in the company.
But he was hired for a reason. He had been successful on similar projects at two different companies and came with credibility. Transparency is what the company needs, and he was ready to bring it.
So what we looked at was how he would approach sharing his message and we did that by role-playing his conversation with the VP.
His first attempt:
“You asked me to analyze the data and I did that and I will have to walk you through some scenarios that will break original ideas. There were two mistakes made in previous analysis; the market size, and the market penetration.”
How do you feel about his first delivery?
One observation is that there are some words that invoke strong emotions: “You”, “Break”, and “Mistakes”. I can almost visualize a person hearing these words and tensing up their shoulders, bracing for the impact of more bad news.
The second observation is that Jason is taking a “telling” perspective, rather than a “collaborative” perspective. When you “tell” someone something, it makes them feel like they either have no other options or they need to be defensive when sharing an alternative perspective. When you take a “collaborative” approach, then it empowers people to feel like part of the solution.
Instead of leading with the problem, Jason decided to shift the goal to be about investigating more information from the VP.
In other words, he reframed his goal of opening the conversation.
His second attempt:
“I have analyzed the data and I have information about X, information about Y, and I notice that I’m missing information about Z which is 30% of the projection. Could you share with me what this 30% was about from the previous leader?”
The reason why this approach is helpful is that there is an opportunity for the VP to fill in some gaps that Jason has about the situation. For example, maybe there is another investment account that Jason was unaware of as someone who is new to the company.
And in the circumstance that the 30% is indeed missing (which is what Jason will assume when going into the meeting), he can segue into this next bit:
“I see, so given that this 30% is unavailable for this project, I have a few scenarios we can walk through together about how to move forward. As you can see, not having access to that 30% will impact the direction of the project, so we will likely have to reset some expectations.”
How does this second attempt feel to you?
It’s more collaborative. It’s inquisitive. It’s rational. It prepares the person for a conversation, not a bomb.
Jason had reframed his approach from being the “bearer of bad news”, to being the “investigator” and “consultant”.
What can you take from Jason’s experience to help you in high-stakes conversations?
*Names and elements of the scenario have been modified for privacy purposes.