⭕“Just circling back on this”

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Welcome to The Thinker, a twice-monthly newsletter where I provide thought-provoking questions to help you cultivate a fulfilling and high-performing career.

Hi there!

Happy New Year! We’re kicking off 2025 with a topic that’s near and dear to every high performer’s heart: getting buy-in from key stakeholders. 

We spend so much of our workday trying to get other people to do things for the betterment of the team and organization. Whether it’s just trying to move obviously important initiatives and projects forward or getting clear on a decision, it’s often harder than it should be. 

It can feel like pulling teeth when trying to bring others along and support our work. It looks like Slack messages that are consistently left unresponded to, emails that we’ve bumped three times, meetings where it feels like we’re talking in circles with key stakeholders, only to end the conversation with no resolution.

That’s why, today, I’m sharing some non-traditional thoughts on how you can align key stakeholders. Cozy up, and let’s dive in ⬇️

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1. Is what you’re working on actually important to the stakeholder?

→ If they give you their time, will they be more successful in their role?

→ Do they have anything to lose by not responding?

The number one reason why you’re struggling to get buy-in might actually be because what you’re asking them to opine on isn’t that important, at least not for them. Your first order of business is to take a step back and really consider how your work fits into their goals and their success in the role.

If it’s mostly one-sided, and they’re primarily just a blocker to you getting what you need, then it’s time to take a step back. Two options here: get creative on re-carving the pie so they get a “win” by supporting you and/or turn your focus to removing as much friction as possible. Hence our next point…

2. Are you being clear as mud?  

→ Are you tailoring the modality (e.g. Slack, email, meeting) to the person and the conversation?

→ Is your communication skim-able?

Everyone learns differently, and thus everyone consumes information and processes it differently. Some folks just don’t actually read their emails. Some need to talk at you to process what you’re asking and give their thoughts. Improve your efficacy here by asking your stakeholders how they consume and process information best and also look for patterns where communication with them has been successful.

Then, as a learning exercise, look at the last time you communicated with them in a written format. Open the Slack, document, or email on your phone and see if you can absorb and process in a small screen with a quick skim. If it takes more than a few seconds for you to orient yourself and read, even with all the context you have, then you’re making it too hard for them. You need to simplify and reduce friction.

3. Is there a benefit to them not responding?

→ Are they trying to avoid a written commitment?

→ What could you change to make it feel “safer” for them to align with you?

As a recovering people-pleaser, it took me a long time to realize that people might not respond on purpose. Sometimes it’s not actually because they’re too busy, or because they “didn’t see your email,” but rather because they saw it and had a reasonable reason to avoid it.

Maybe you’re trying to get them to align on a decision that they actually don’t feel is the right decision, but they don’t know what to do instead. Or, maybe, they haven’t told you yet, but they think whatever you’re working on will backfire and they don’t want to be in direct association. Be thoughtful here about what they have to lose by saying yes, and identify a way you can strategically go around them (if it is for the betterment of the organization), or bring them along differently (the better option, since you’ll get yourself an ally for life!).

I know that it can be really frustrating when you aren’t able to move things forward because you’re getting blocked by people left and right. As always, start your strategic work by assuming good intent and having strategic empathy about why they might be choosing avoidance. When you take a step back and zoom out, you’ll find more efficient ways to get things done.

Cheering for you, 

McKay