Part II: Derisking 12 common workplace scenarios

How to identify and address risks in situations like: giving constructive feedback, sharing a controversial idea, doing cold outreach, and more

👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, career growth, and standing out as a high-performer.

We’ll cover simple ways to derisk these workplace scenarios below:

1. Sharing an idea your colleagues might find controversial

2. Giving constructive feedback to a direct report

3. Testing your offer

4. You made a mistake and need to tell your customer

5. Troubleshooting a technical issue

6. Giving feedback to a peer

7. Presenting to your CEO and leadership team

8. Getting a bug resolved quickly

9. Giving your manager a project update

10. Pitching and cold outreach

11. Raising the price of your product

12. Delegating to a team member

Read time: 6 minutes

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This is Part II of a two-part post. See Part I: How to identify and reduce risk in your daily work.

When I’m feeling worried at work, it’s often because something seems uncertain.

I’ve found that trying to fill in the blanks and get more understanding usually makes me feel better.

Marie Curie said, “Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less.” I like this quote. She was probably referring to macro societal issues and being a good citizen, but this applies to anxieties at work too.

Last week, I wrote about how to identify and address risks. The gist is to ask yourself:

1. What’s the most obvious thing that could go wrong? 

2. What can I do to reduce the chances of this happening?

With these two questions, you can keep it simple. It’s easy to remember and applies to a range of situations.

This week, I want to share examples of what derisking looks like in a variety of common scenarios.

⛑️ Welcome and thanks for being here! If you’re looking for a sparring partner and external perspective, I typically work with tech leaders on: Managing up to a CEO/SVP, strengthening your executive communication, framing your ideas, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.

1. Sharing an idea your colleagues might find controversial

• Situation: You’re sharing an unconventional idea and you might get pushback.

• Obvious risk: Your audience may misunderstand you. They may think you mean one thing when you mean something else.

• Action: To mitigate, you can add “to be clear” to your post to prevent confusion. “To be clear, I don’t mean X.”

2. Giving constructive feedback to a direct report

• Situation: You’re giving hard feedback to a direct report.

• Obvious risk: Your direct report believes the feedback is unwarranted, so they don’t change. Or they say they understand, but inside, they feel deflated and aren’t as motivated to do their best going forward.

• Action: To mitigate, think about the situation from their perspective. For example, they feel threatened because they don’t think you’re on their side or the news you’re sharing feels like a demotion. Once you know this, you can craft your script so it’s clear that you very much believe in them, you focus on strategy not self-expression, etc.

3. Testing your offer

• Situation: You have an idea for a new product or service, but you’re not sure how your prospective customers will react.

• Obvious risk: The offer you’re betting on isn’t right.

• Action: To mitigate, instead of sending to all 15,000 leads at once, you can send it to a smaller first batch to see how they react. This way, you don’t “waste” 100% of eyeballs on non-optimized messaging—you can iterate, then can apply learnings to the next group.

4. You made a mistake and need to tell your customer

• Situation: You made a mistake that affects your customer.

• Obvious risk: The customer gets upset and decides to cancel their contract.

• Action: To mitigate, you should be accountable AND avoid making the situation sound worse because they might get even angrier. Frame to minimize the impact while being honest.

5. Troubleshooting a technical issue

• Situation: You’re explaining your problem to customer support. 

• Obvious risk: You explained everything in detail, but they transfer you to another agent who asks you to explain it all over again.

• Action: To mitigate, copy/paste to save what you wrote so you don’t have to type it all from scratch. Or have a concise 1-2 sentence explanation ready if you’re sharing verbally. “I’m having an issue with X, and I would like to be able to Y.”

6. Giving feedback to a peer

• Situation: You want to share feedback with a colleague at your level.

• Obvious risk: They’re shocked at how you’re overstepping. They believe you’re not in a position to be giving them this kind of feedback, and you need to back off.

• Action: To mitigate, explain that you’re sharing the feedback because you care about them and you’re trusting that they’ll take the feedback knowing it’s coming from a good place. Offer your observation and the impact of what they’re doing. Try to set a positive emotional tone—don’t be heavy or somber about it.

7. Presenting to your CEO and leadership team

• Situation: You’re presenting your team’s proposal in a high-stakes meeting. 

• Obvious risk: The presentation goes poorly. You prepare material the stakeholders don’t actually care about. The executive team has many questions and you are trying not to get overwhelmed.

• Action: To mitigate, run your points by a few stakeholders before the meeting to make sure you’re aligned and have allies. Think of the most obvious questions the leadership team is likely to ask.

8. Getting a bug resolved quickly

• Situation: You encounter a tech issue and want to submit a support ticket.

• Obvious risk: The customer support team doesn’t have enough context and can’t replicate the issue to troubleshoot. If you don’t share enough information, they will need to follow up, which slows down the process.

• Action: To mitigate, make a Loom video of the issue and share details of your computer/browser version. When you proactively share this, you help them help you. This might seem like a minor example, but it represents a whole category of small-ish things you can easily do to reduce unnecessary back-and-forth.

9. Giving your manager a project update

• Situation: Your manager asks for an update on your project.

• Obvious risk: They think you’re meandering, they have to wade through too many details, and they don’t know what to pay attention to or how to support you.

• Action: To mitigate, put your main point up top, and context below. Be explicit about what you need from them. Share potential risks (this is meta, I know) so they’re in the loop and know you’re thinking about the project strategically.

10. Pitching and cold outreach

• Situation: You are sending a cold email.

• Obvious risk: Your recipient doesn’t see why your product is relevant, and they think you’re spamming them with a spray-and-pray approach.

• Action: To mitigate, mention why you’re reaching out to this lead specifically. Focus on their goals—not on your mission, vision, product, etc because they don’t care (yet). Trim anything me-focused, and be as you-focused as possible.

11. Raising the price of your product

• Situation: You are raising prices and need to communicate this to users.

• Obvious risk: Customers are upset that the price is increasing, so they cancel and churn.

• Action: To mitigate, try to put the increase in context and make it sound small. This is something the Zoom team actually did—I got an email from them a few weeks ago that prices were going up. Their email mentioned, “It’s only an additional $1.24/month” to show that the increase isn’t much.

12. Delegating to a team member

In Part I, I wrote about the risks when delegating to a team member. A newsletter reader, Justin Lewis, shared this fantastic example:

• Situation: You are delegating a data collection project to your direct report.

• Obvious risk: They collect 130 examples of data…but don’t collect the right information or gather data on fields you don’t need.

• Action: To mitigate, check-in after they do a few entries. This surfaces unknown unknowns early in the process, so you’re aligned and they can work efficiently.

By the way, when you ask yourself “what’s most likely to go wrong?” you can answer this question on different levels. The level I suggest for this use case: “My junior team member might spend too much time going in the wrong direction.” You don’t need to list all the specific ways they can make a mistake—to Justin’s point, it would be an overwhelming list.

So in a situation like this, the act of checking in early and building in feedback loops is derisking.

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More news from the community

I’m not an affiliate for the below. These are simply recent launches I thought you might find interesting:

• My good friend Tiago Forte is running his Second Brain Summit on October 3-4, 2024 in Los Angeles. The last day for early bird pricing is today (August 21). Tiago is a rigorous thinker, fellow writer of long-form essays, and community builder who I’m grateful to know. If you’re excited by knowledge management and the concept of a “second brain,” this is a good chance to meet like-minded folks.

• Another good friend is clinical psychologist and New York Times bestselling author, Dr. Becky Kennedy, who recently launched the Good Inside app to help busy parents raise study, confident, resilient kids with personalized advice based on your child’s age. I’m obsessed with Dr. Becky’s Instagram—even though I’m not a parent, I love her advice for talking to my inner child. If you’ve ever thought, “I wish I could be there for my 5-year-old self,” you can do it now as an adult.

• A few weeks ago, I had the privilege of going on the Hubspot podcast with Hubspot’s CMO Kipp Bodnar and former CMO of Zapier, Kieran Flanagan. It was fun to talk shop with fellow marketers—and I love how both of them are hands-on leaders who value IC work and the craft of marketing. Check out the episode on YouTube or Spotify:

Timestamps:

• 00:00 Partnering with Seth Godin

• 04:27 How I rewrote Airbnb’s ads when they faced city opposition in SF

• 06:31 Embracing iteration and doing more reps to improve at your craft

• 10:25 Distinguishing strategy vs strategic thinking

• 15:08 Working with Seth was transformative, raising standards

• 18:02 How can a manager increase team standards?

• 19:38 High standards but low coaching (2x2 matrix) leads to sink-or-swim culture

• 23:51 Leaders must stay close to primary data for better judgment

• 25:51 Why we need more senior tacticians

• 31:40 Exploring “being direct” really means (it’s not freedom to be rude)

• 36:46 Encouraging critical thinking through specific questions

• 40:59 Leaders must embrace “positive confrontation” for growth

• 43:08 Feedback requires strategic communication

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Do you have an example of derisking in your work? Hit reply or share in the comments.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

PS Here are more ways to connect:

1. Follow me on Twitter or LinkedIn for insights during the week (free).

2. Check my availability to do a keynote for your team.

3. Work with me for 1:1 executive coaching. I find it extremely rewarding to give personalized guidance to ambitious operators. My current clients include leaders at startups funded by Sequoia, Accel, Bessemer, SV Angel, Kleiner Perkins, etc.