Emma: Recently, a good friend and longtime reader of The Bent got this writing test as part of her interview for a new job.

Imagine you received an email from a business partner who disagrees with your approach, and you need to help them align with it. Write a response email justifying your recommendation.

Andy: I kind of dig it! I love the idea that a place is curious about how I’ll interact with my ideas, and not just what those ideas are.

Emma: Especially because writing this exact email is a regularly recurring responsibility at lots of our jobs, but I’ve never been quizzed on it during an interview. I think it’s pretty cool, and also frustrating because of course IT DEPENDS — on who the business partner is, what they care about, how much power they have, how much knowledge they hold, the level of trust we have, on and on.

Andy: Absolutely. Any kind of hypothetical question in an interview feels like a trick. There’s so much missing context. I have so many questions.

Emma: Which the hiring manager knows. That’s not really the point of this prompt. The point is: Can you write a persuasive email without any red flags?

Andy: Of course you can! You’ve been writing better emails with us for long enough that you shall not be stymied — even though this one is tricky. I’m not a huge fan of dealing with this level of deep thinking over email.

Emma: The most challenging part for me is how much to include — like, the literal number of words. I need to sound knowledgeable, I need to prove that I’ve thought through my approach, I need to get them on my side. This prompt is begging for paragraphs, and attached decks, and see Appendix C’s, but we all know that nobody is convinced by long explanations.

Andy: Red flag! More is not more here. Believing you can be convincing and simultaneously concise might require a shift in mindset. I’ve had to train myself out of my knee-jerk thinking: I hate them for asking this question! Why do they doubt me?! They’re out to get me! Now I have to write a giant thesis!?

In reality, the bulk of any doubt is coming from my internal critic. I force myself to hear the question in a friendlier, more curious tone, even if that’s not how it’s written. When I can do that, I turn from defensive fool to thoughtful scientist. I have a theory, a hypothesis, and my research. I’m more than happy to outline them all for inquiring minds.

Emma: Same, same, but different for me. I’m more apt to immediately question my approach and start negotiating against myself — another red flag. I have to tell myself: “Oh, poor Sandy! He doesn’t know what I know.” If I can treat this business partner’s email as confusion, I’m simply explaining. No need to fold.

Andy: Your mission is to go into this email confidently. Appreciate yourself for having a point of view, and know that you got to your conclusion for a reason. Paint it all with trust that the person on the other end is also swayable by your sound judgement and wants what you want: a successful outcome on whatever this assignment is.

Emma: However much we’d all like a one-and-done email exchange, in the real world, there’s probably going to be some back and forth. I’m all for flexing to accommodate other, smarter, more effective points of view. Stay open to new ideas, and know that there’s plenty of time to learn and revise your thinking.

How to Write an Email That Gets Someone On Board

Prep-Work to Support Your Point of View

The argument for your approach might already exist, fully formed in your brain. This is especially likely if you’ve spent a lot of time developing it, or have talked it through with your team or your boss. Often, though, we’re operating on instinct and a persuasive point of view will need a bit of excavating. It’s definitely in there. Our first step is to open a blank doc and in a gentle, open-minded tone, ask:

    • What is my recommendation?
    • Why do I think it will work?
    • What alternatives have I thought about? Why aren’t I going with them?
    • How will I pivot if my recommendation doesn’t get the results I’m expecting?
    • Why might someone want to try something else? Could I get behind that?
    • How locked in is this decision? How flexible am I? How flexible is the boss, the project, etc. to changes?

Review Your Scorecard

From there, we’d whip out a scorecard of the key targets we want to hit with this email. Here’s what’s on ours — feel free to create your own.

I assuredly explain my reasoning. I don’t negotiate, offer to collaborate, or ask for permission. Not yet, at least. Compromise or collaboration may be necessary, but all you’re doing right now is simply letting this person in on your decision-making process. You’re not asking for permission. You’re helping them catch up.

I include no more than 3 points; 1 is also okay. Ideally at least half of these points ladder back to things we all agree on (e.g. a directive from the top, core values, business goals) and/or can be bolstered with numbers, documentation, the handbook, etc.

It’s easy to read and not visually overwhelming. White space! Short sentences! More bullets!

I save pleasantries and offers for further discussion until the end. In this email and every email, always amen.

Start Drafting

Remember, keep it short, confident, and pleasant. Here are a few examples in a few different lengths and tones that still fit our criteria. Which style do you think our reader should have sent in with her writing test?

Three Reasons Why With Glorious, Beautiful Bullets

Hi Kyle,

We’re making a change in our process for three reasons:

– Improving turnaround time. Our KPI for the year is to decrease turnaround time by 50%. This will allow us to do more work, more quickly, without increasing our team size. For the business this means we can expand to new markets without hiring or expanding our team budget.

– Retaining quality. While our turnaround time goal is halved, our quality aim is to stay with 10% of our quality today. We accept that we may take a small quality hit to reach our turnaround goals, but no one’s willing to take a large hit. We’re prioritizing changes that reduce turnaround with very little impact on quality.

– Easing in and checking our assumptions. To start, only 10% of the team will be using the new process. We’ll be carefully monitoring our turnaround time and quality metrics to make sure that our hypotheses are true. If our quality dip is above 10%, we’ll stop and try something else.

We’re hosting a lunch and learn on Tuesday if you’d like to learn more about how we got here. I’ll be there and so will sandwiches from Giordano’s.


One Reason, Plus a Few Breezy Supporting Sentences

Hi Sandy,

We developed this subject line to align with the tenets of the featured brand: bright, off beat, and minimalist. Since this campaign is targeted to customers who have indicated interest in the brand, we’re anticipating it will resonate, and meet or exceed average open rates.


Short and Sweet

Hi Nora,

We launch on The Bent on Tuesday mornings because it’s best for our upload schedule. Monday sends = Sunday evening work. No fun.

Thanks for the question!
Andy + Emma

Run It By Fresh Eyes

The final step in crafting this type of communication is to pass it by a colleague or two before sending. Since this email is acting as a mini persuasive essay, it will always benefit from an outsider brain’s perspective. Show them your scorecard, but don’t walk them through your thinking. Let the email do it. Gather your feedback and adjust as necessary.

Then hit send. You got this!