💜 Ensure your place at the strategic table in 2026

Hello and Happy Thursday!

HR deserves a seat at the executive table. Period. Hard stop.

While this is becoming more common in the workplace, it’s (sadly) still not a given - oftentimes because leadership still sees the function as compliance and precaution-focused, rather than strategic.

So how do we shift that narrative? I used to think it meant bringing the most strategic people-priorities to the discussion. Now, I’m a full believer that understanding the needs and strategic views of the entire leadership team is a more effective approach.

Why?

Because when you understand everyone’s unique challenges and viewpoint, you become part of the discussion instead of fighting for airtime. And you can clearly articulate how your projects and priorities could help them meet their goals.

Everyone wants someone at the table who can help them achieve what they’re setting out to do.

The question becomes: How the heck do you learn what’s keeping your leadership team up at night?

The answer is, you ask.

That’s why today’s issue is dedicated to how you can hold a leadership listening tour that will set you up as a powerful ally and executive partner in 2026.

To getting curious,

Jill

Slowing down to see the bigger picture

There is no one I have more grace for than an HR person who has to cancel a call at the last minute. Working in HR pretty much guarantees you are in the center of whatever fire has emerged that week. {insert examples of fires to be dealt with}

While I used to thrive in the ever-changing landscape that came with my Head of People role, looking back, there’s one thing I wish I’d prioritized: listening. Specifically, taking time to sit down and really listen to what was on my executive team's minds.

No survey.

No half-day working session.

Just taking 60 minutes to individually connect, listen, and build relationship with each member of the leadership team. Especially this time of year, when both reflection and planning are top of mind.

What is a listening tour?

A listening tour is exactly what it sounds like: a structured, proactive effort to gather insights. While they are often discussed as a method for collecting employee sentiments, I think they are VASTLY underrated when it comes to really understanding what’s keeping your leadership team up at night.

This does not have to be fancy. I repeat, this does NOT have to be fancy.

In fact, I’d strongly argue for keeping it casual, because that’s when the best insights emerge. The goal is to make it feel less like an "HR initiative" and more like "a colleague who wants to understand how I can be useful to you.” Because that’s really what this is all about!

Why spend time on this - especially now?

Like it or not, Q4 is prime season for both reflecting and planning, making it the perfect time to inquire.

Your CEO is likely thinking about how to recap the year to the board and what the organization's biggest areas of opportunity and risk are going into the new year.

Your Chief Product Officer is coming to terms with what parts of the 2025 roadmap won’t get finished before the holidays, automatically pushing into the new year.

And your Head of Sales is strategizing on how to close those last few deals, while also using this year’s data and market conditions to forecast what’s possible heading into 2026.

Believe me, the last thing I want to do is put another task on your list while you’re navigating open enrollment, end of year reviews, and (oh yeah) planning that holiday party you were somehow tasked with throwing.

I’m sharing because I know the time you’ll spend meeting with the leadership team will have some of the highest payoff of anything you could prioritize in these last weeks of the year. This payoff might be:

• Strengthening (or beginning to form) genuine relationships with each leader

• Understanding things about them and their role that had never occurred to you before

• Being able to connect dots and articulate patterns that others have yet to identify

• Equipping yourself with the information you need to directly align your desired 2026 initiatives with solutions to your colleagues' biggest challenges

How should I approach busy executives with this ask?

It’s possible you already have a strong bond with each member of the executive team and asking for time to connect won’t seem unusual. However, for some, this may be the first time you’re approaching members of the leadership team about having a casual 1:1 conversation. If that’s the case, here are some things to keep in mind when you reach out:

1. You want this conversation to feel authentic and relational. The last thing you want is them fretting over why you’re asking for the time. Yes, they’re senior leaders, but the “HR needs to talk to me” triggers can run deep. If you’re worried that they’ll see this as more than a chance to connect and learn, call out that tension specifically before you meet.

2. Aim for an hour - but be OK with 30 minutes. We have zero doubt everyone on your team is busy. But this time will also be a chance for them to reflect. Unless 60-minute meetings are unheard of in your company, I strongly recommend asking for the full hour. Having the time will allow you to ease into the conversation versus needing to dive straight into questions. Besides, wrapping up early is always better than them needing to cut off a super critical conversation to make their next call.

3. Set the stage, so they know what to expect. No, I don’t think you should send a calendar invite with an agenda, but it's important for them to understand the intention behind the ask. If you’re at a loss for words, here’s a message you can swipe and customize:

   “Hey [Name]-

   [Casual intro, such as: I hope that meeting with Acme went well earlier this week! Sounds like it might be a great partnership.]

   I’m reaching out to see if you you have an hour sometime in the next few weeks to grab coffee / hop on a call / [whatever fits your culture].

   As we close out the year, I’m trying to better understand what each leader on the executive team is focused on heading into 2026. I realized recently that I haven't spent enough time understanding what each of you is wrestling with day-to-day. I’m most helpful when I understand what success looks like from your seat.

   I’ll come with some questions, but really just want to listen and learn. No agenda, just want to understand your world better.

   If you’re open to connecting, let me know what time works best for you!

   Cheers, [Name]

4. Be OK with a no. In a perfect world, each executive would enthusiastically make time to connect. In reality, you may find that some aren’t able or willing to meet. And that’s OK! Start with anyone who is excited to connect. The hope is that the remaining leaders may be more open to your ask next time around, having heard from their peers that it was a great, productive chat!

What questions will get them talking?

Once you’ve got some enthusiastic yeses, it’s time to move onto the really fun part - the questions! What you ask is completely up to you, but here are some juicy questions we’ve round tested and can assure will start some great conversation.

Ground the conversation (2-3 minutes): "I'm spending time with each leader to better understand what you're focused on and where you're feeling friction. I want to make sure I understand the business from your perspective."

Their world (10-12 minutes):

• "What's on your plate for 2026? What are you being measured on?"

• "What's working well right now that you want to protect or scale?"

• "Where are you feeling stuck or slowed down?"

• "What trade-offs are you wrestling with?"

This gives you the full landscape - operational challenges, resource constraints, team conflicts, market pressures, etc. People issues will naturally surface here (they always do), but you're not forcing them into an HR box.

Understanding constraints (5-7 minutes):

• "What would unlock progress for you?"

• "If I shadowed you for a week, what patterns would I see that frustrate you?"

• "What's the gap between where your team is and where they need to be?"

Close (2-3 minutes):

• Reflect back themes: "So it sounds like speed to market is critical, and you're concerned about..."

• "What else should I understand?"

• Thank them for their candor

The shift this creates: When the conversation is more casual and driven by curiosity, it’s way more likely that you’ll leave with real, vulnerable insights instead of high-level soundbites. You can then connect the dots to how talent, culture, or organizational design can help and find ways to truly partner in the new year.

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