Skip-level meetings in smaller companies
A co-founder of a company with less than 150 people recently asked me, "Should I run skip-level meetings, even if our company isn't super large?" Here was my answer....
Earlier this year, I was asked by an executive of a company with less than 150 people:
Should I and my co-founder run skip level 1:1 meetings?
We’re not a super big company – but my co-founder has insisted in wanting to meet with my direct reports. I’m concerned if the team will get mixed messages with these cross report 1:1s, and that these meetings aren’t that efficient to begin with…
What is ‘normal’? And what is an effective way to run skip-level meetings in a smaller org?
✨ As a fun note, this executive submitted this question through our Coach feature in Canopy – where you get direct access to me Claire, CEO of Canopy, and our coaching team. We respond to your written leadership question within 72 hours ✨
Here was my response…
Usefulness is proportional to purpose and preparation.
Yes, 1:1 skip level meetings can be useful even in small organizations.
However, like any meeting, they only are useful if there is real purpose and preparation behind them.
As a result, to ensure this efficacy, you'll want to focus these skip level meetings on three primary areas:
Uncovering issues.
Building rapport and organizational alignment.
Gaining greater visibility and new ideas that can help grow and further the organization.
That being said, if you haven't found these meetings with your co-founder's direct reports to be effective so far, I have a few suggestions that you can try (if you haven't already)...
Focus on asking questions that give you insights to your functional area.
For example, if your functional areas is “Product,” you could ask...
Any learnings from your own day-to-day work that impacts the product?
Any insights from customer interactions or your own usage of the product?
Any ideas, suggestions, or concerns with the product roadmap, etc?
What opportunities do we have to improve the product?
Is it clear how your day-to-day work contributes to the product's success and overall company's success?
Is it clear what direction the product is headed, and why we're making certain decisions about the product?
Use the time as rare opportunity to gage morale.
Ask questions to understand what issues they might have, and so then you can circle back with your co-founder to gain a more complete picture of how your team is doing.
For example, you can ask questions such as:
How is your energy level these days?
How clear is the overall direction of the company?
How is the working dynamic in the team?
What are things you see opportunities for improvement for myself and/or the co-founder?
Frequency is set in relation to your findings.
If you feel you already have a good handle on the answers to these questions above without holding skip level 1:1s, then I might recommend scaling back the frequency of the skip levels to be say 1X per quarter or 2X per year, rather than 1X per month.
The frequency of your meetings should increase if you feel you do keep getting vague or avoidant answers to the questions above.
What is ‘normal’?
For an executive of your size of organization, it's normal for them to want regular 1:1 touch points with every member of the organization, even if it's not their direct reports – so know it's not an unusual request. It sounds like he or he may be insistent on skip level 1:1 meetings because (1) they personally would like more visibility into the organization and/or (2) they've been finding it helpful as a way to align the organization, communicate company vision, and hear issues firsthand.
However, it may be worth having a conversation directly with your co-founder to level-set on expectations of: Why are skip level meetings important to them? What is your co-founder hoping to learn? Perhaps there is a different reason your co-founder is wanting to hold these meetings, and there is a gap in understanding for you two to close.
Either way, discussing the shared purpose and methodology of the 1:1 meetings can help you both be on the same page as to the purpose behind these meetings and broader company management.
If you haven't already, I'd highly recommend visiting the “How to Run Effective 1:1 Meetings” in Canopy – and perhaps even use that as a common touchpoint for you and your co-founder to anchor your discussion around for "how we should be doing 1:1s at our company.”
If helpful, for an organization of your size, I'd say I most commonly see an executive hold skip level 1:1 meetings every other week or 1X month with folks who are not their own direct reports – but it of course depends on the degree to which those meetings are in service of your business.
What about “mixed messaging” in a smaller organization?
Lastly, to address your concern that there may be "mixed messaging" when there are 1:1 skip levels happening in small team – know that this is not a bad thing :-) That is, your team likely already receives "mixed messaging" from you and your co-founder on a day-to-day basis in meetings, write-ups etc.
This is merely the natural byproduct of being two unique individuals. And so the fact that you have regular skip level 1:1s – where you can ask your team members, "Hey what do you think?" – acts as a forcing function for you and your co-founder to confront that you might be having different messages, and get direct feedback from your team on these differences.
In other words, skip level 1:1s can help reveal these differences to you faster, so you can then address them faster. (And, for what it's worth, the "mixed messaging" problem only increases the larger the organization gets, and so it's helpful to set strong habits around this now, rather than later.)
Hope this helps. Look forward to hearing how you decide to move forward!
-Claire
👋 Keen to have me answer a specific question you’re facing? Become a Canopy member 🌿 and access our Coach feature for direct line to me and our coaching team.