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Critical Conversations: Why They Matter

How do you know when something an employee did requires more than just sharing what didn’t work and actually requires a deeper dive with the employee, a critical conversation? Remember that by critical, I mean both vitally important and involving a critique of behavior.


There are four key elements to look for when determining whether you need to have a conversation with the employee instead of giving direct feedback.


Something is at stake.

Stakes are high for you, your employee, the company or all of the above. This is when there is a risk of losing a client, missing a major deadline, of delivering low-quality work—when there is some serious risk that needs to be addressed.


There’s an impact if nothing changes.

What will happen if things keep going the way they are going? If something needs to change, that’s when a conversation becomes critical. For example, if an employee keeps coming to meetings with no set agenda, the impact is that you’ll continue to have meetings that aren’t productive. More importantly, it sends a signal that, as a leader, you really don’t hold people accountable.


Action is required of both parties.

If you’re the one holding a critical conversation, you’re likely asking someone else to change. Although this is often the case, change coming from a critical conversation is not one-sided. This one is usually harder for people to understand.


If you are asking someone to change something about the way they work, treat you or interact with a fellow employee or client, something is required of you as well. It might be the way you support your employee, or it could be how you hold the employee accountable when he or she doesn’t make the agreed-upon change. Either way, there is something required of both parties involved in the critical conversation.


It’s a conversation.

A critical conversation is not a demand, it’s not an admonishment of the other person and it’s not an ultimatum. It’s a conversation between two people; this means it’s two-sided. It means it’s not just about sharing your perspective on what didn’t work; it’s also about listening to the other person’s perspective, about hearing their point of view and about coming to an agreement together. That’s why it’s called a critical conversation — not a warning meeting or a reprimand or negotiation.


Here is a set of questions to help you determine if you need to have a critical conversation.


• Is something at stake?

• What’s the impact if nothing changes?

• Is action needed from both parties?

• Is it a conversation or ultimatum?


We rarely notice the impact of not having a critical conversation immediately, although the repercussions of avoiding it can haunt us for weeks or months. A client of mine — let’s call her Emma for the sake of anonymity — hired her first chief sales officer, Jake, to help her team grow to the next level. Jake was the highest-paid employee on the team, and Emma was excited to have him as a part of the team.


In the first few months, Emma started to notice in meetings how Jake would not listen to the client’s ideas but would deliver what he thought was best. This went against Emma’s philosophy of listening to clients and serving their needs. She was irked by these meetings but said nothing. Over the next several months, she continued to notice instances when Jake was not communicating well with the other departments, taking a me-first approach, and taking credit for work his team delivered without recognizing the team. Emma was furious with the way Jake, her top hire, was acting as a leader for the organization.


When I asked Emma if she’d shared this feedback with Jake, she paused, blushed and doggedly admitted she’d not shared any of it. Instead, she moved Jake off their biggest clients and tried to protect the team from his interactions. She’d been watching from the sidelines as Jake was unknowingly dismantling the culture she had worked so hard to create, too afraid to speak up. She started to see her executive team look at her in a different way. They were all complaining about Jake and wondering why she kept someone on the team who clearly wasn’t a fit.


Emma finally realized the error of her ways and held a critical conversation with Jake — six months too late. The result of the conversation led to Jake and Emma agreeing on action items to take. A month later, after he didn’t meet any of them, they parted ways.


What was the impact of Emma waiting six months to have a critical conversation? In the immediate term, she paid six months of top salary to an employee whose value didn’t match the pay. She had to stretch her other employees to compensate for Jake’s limitations, and she denigrated her values by not taking action when Jake violated those values. It wasn’t until after she let Jake go that she felt the difference. Immediately, the productivity of her sales team exploded, landing new client deals and delivering great work. She promoted Ranelle, the employee below Jake, to a director-level position and noticed that she didn’t need a chief sales officer at all; Ranelle could do all of Jake’s work and more.


It wasn’t until two months later, though, that Emma took the ultimate blow for her lack of urgency in having a critical conversation. Two months into her new role, Ranelle put in her notice. She was leaving, and when Emma asked why, she said she’d been in talks with a competitor for the last four months. She’d had enough of working for Jake and an organization that promoted selfishness, and she had decided to look elsewhere. Emma not only lost six months of her team producing at a high level, but she now lost a key employee, all because she didn’t have the conversation she knew in her gut she needed to have.


What critical conversation have you been putting off?



Originally posted in Forbes on 4/28/20

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