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February 10, 2020
Kate Marshall

How to talk to your boss: 10 tips for communicating with executives about HR needs

HR changes on a dime—it always has. There’s a misconception that HR practices are outdated or under-updated and in ways, that can be true. However, you know better and so do we.

HR is at the mercy of constant technological change and a constant flux in the way job seekers browse and candidates apply. Work and life are so inextricably linked, in fact, that HR generalists must be adaptive to net-new expectations of the work-life balance year over year, while new HR specialists are hired quarterly to add new functions to the team.

With this constant revolution in the industry and the assumption that HR is behind the times, it’s no wonder that you’ve got a disconnect in your company. Your C-suite executives are under-informed about the nuances of HR and may not know to center future-focal HR initiatives like employer branding or culture. Meanwhile, your employees and candidates recoil at your untouched cultural issues and clunky processes.

One day, you’re going to come to work and face a barrage of HR frustrations and un-bridged workplace gaps that inspire you to make a plan. Your plan will be brilliantly lit and structurally sound... but nobody will want to listen (let alone be convinced).

10 tips for talking to your boss:

Step one: Pick your target exec

A big part of approaching conversations with your leadership team is knowing who handles what.

For smaller companies, your executive team may consist only of a founding CEO or a small oligarchy of decision-makers—while larger enterprise teams might report to multiple C-level executives. In that case, it’s important to know who is most informed and equipped to handle your request or idea. 


Your Chief Executive Officer will be interested in any and all facets of the business. However, it’s wise to show restraint when chatting up your CEO—since they’re forced generalists with a lot to focus on, they may not be the core decision-maker for your more narrow or specific concerns.


The Chief Financial Officer will, of course, prioritize all things financial. CFOs must stay overtly data-driven, hyper-focused, and unimpressed when the conversation turns too emotional. Do you hope to get budget approved for a new HR endeavor or an increase in a particular salary set? Approach your CFO.

If you do, bring data. For example, remind them that the company loses around $15,000 for every employee who leaves unhappy—so an extra budget for rewards & recognition should be no big deal.  


Your Chief Marketing Officer centers their work on your company reputation, how you gain traction with an audience, and efforts to bring in qualified leads from a variety of tactics. They overlap with HR on culture and how things like employer brand and reputation could hinder (or improve upon) their campaigns.

To marry your unique points of focus, remind your CMO that more than 60% of customers reported a refusal to buy from brands with known employment and culture issues. An extra tip for communicating with executives in marketing is to position HR as a function of the brand.


In many companies, the Chief Operations Officer is part of the HR function or team. For other companies, Operations and HR are distinct. In either case, your COO focuses on how people operate, the morale and work ethic of the team, and the tools and resources allotted to further optimize those things.

You’ll have an easy time approaching and communicating with your operations executive if you’re ideologically aligned. Discuss the impact of culture and job satisfaction on productivity and collaboration; remind your COO that without a positive working culture and a sense of purpose, employees are more likely to underperform and then leave. 


This one is tricky. Most companies with a CTO have a Chief Technology Officer—someone interested in your project or concern as it pertains to your need for physical or digital assets. For others, CTO can also refer to a Chief Talent Officer or Chief Transformation Officer, both of which would have inextricable links to HR, and a modern opinion on workplace culture.  


If your company is fortunate enough to have a Chief Human Resources Officer, you’ll be in good hands and able to center HR concerns more organically. However, you might find that this role focuses more on compliance or recruitment than on culture. Sell them the rock-solid benefits of an increase in focus on the employee engagement side of things and they’ll hop on board.


Finally, your company may have a Chief Brand Officer, one of the most up-and-coming C-suite titles. If so, this person will overlap with you on employer branding*, company reputation, and centering your company’s culture as a facet of its overall public perception. This could be a great foot-in-the-door to present HR concerns to the entire C-suite and rally whole-team support. 

*If you still feel kind of 🤔 about employer branding, we’ve got a no-frills guide!

This list is nowhere near exhaustive. In fact, there are more than 50 C-suite titles of note and many companies add their own spin. If you’re not sure where your C-suite team falls in line, consult your comprehensive Org Chart or add that document to your list of suggestions. 

Step two: Request the meeting

Whether you hope to introduce a new team-building initiative, add smarter perks to your compensation package, or price out culture consulting for your team, you’ll need to warm up the engine before talking to your boss.

Introduce what you plan to discuss via the easiest and best tool to communicate with your chosen executive. If your person prefers email, go that route. If they like Slack, hit send there. Succinctly communicate what you hope to discuss, why you find it important, and a brief synopsis of the data you will be presenting, so your executives know you’re coming in ready. A sample email might look like this:

Hi [Executive Name],

I’d like to grab time on your calendar to pitch a new Employee Recognition Program for our team. ERPs are proven to increase productivity, employee retention, and employer reputation by 44%. I have a suggestion for an ERP that could double our investment in the first 6 months. Are you available this week for a thirty-minute meeting? 


Step three: Know your executive's flow

To better equip yourself for what may be an intimidating or nerve-racking conversation, research your target. Think backward or ask around to determine what kind of meeting style this executive prefers. Consider how they think about business problems and what type of language they often use. Don’t pretend to be them, but find ways to authentically meet them where they are

For example, if your CBO prefers to meet in a room with a whiteboard for notes, do it. Get your person as comfortable as possible and speak their language to side-step friction.

Step four: Set mutual objectives  

C-Suite executives think about business and work differently than managers, administrators, or producers do. Different perspectives add value to the team, but they can also make it more difficult to reach a unanimous conclusion. When you set objectives for this meeting, walk in an executive’s shoes. Just don’t leave your own behind! 

In a recent study, HR managers prioritized employee engagement above everything else while C-suite executives prioritized retention of high-performers specifically. Knowing this, you might propose your employee engagement initiative in the lens of retaining your top talent. This way, both of you will walk away winning. 

Step five: Prepare for "executive brevity"

We’re all busy at work. However, your leadership team must handle a greater demand on their time and focus. If you want to earn their attention, you’ll need a good business-minded reason. If you want to keep their attention, you’ll need to be concise, direct, and expect the possibility of interruptions. 

Step six: Zoom out

You care about the whole company, but especially the HR-specific tasks in front of you. Your executive team cares about the specific tasks each of you must face, but the prioritize the whole company.

To match that focus and talk to your boss in terms that makes sense to them, take a bird’s-eye view. Consider how what you’re proposing will affect everyone—your team members and leaders, partners, and customers or clients.  

Step seven: Communicate relatable solutions

Rebecca has been an HR Manager at XYZ Corporation for 8 years. She watches recruiters and managers lose out on excellent candidates while top employees leave in droves. Rebecca sees the toxic culture at XYZ for what it is. Her pal Louise works across town at ABC Inc. in the same role and has observed similar issues. Rebecca and Louise decide to communicate with an executive at their companies on the same day; Rebecca plans to present the problem and place blame. Louise plans to propose a solution and data to support her claims.

Who do you suppose will earn a more positive response and which company will more quickly solve its issues? By offering data and solutions in a constructive way, Louise will earn buy-in and help ABC Inc. reset its cultural issues.

Want to take it a step further?

Try approaching each meeting with empathy, says Emma Brudner, Director of People Ops at Lola.com. Listen to the podcast episode.

Step eight: Bring data or plan to test 

Many executives operate with the belief that “guessing is expensive”. If you want budget and resources allocated for your initiative, you’ll need proof. If you don’t have access to data that scaffolds your plan, test first to demonstrate the validity of your idea.

Give execs every chance to say yes and as few reasons as possible to assume something won’t work. Of all of our tips for communicating with executives, this one is the toughest. It's also the most important.

Step nine: Get to the point 

When you do get a chance to communicate with the executives at your company, here's a big tip. Make your asks known loud and clear. Don’t leave that meeting resolving to “talk about it again some other time". Know the good, better, and best outcomes and push for those.

Early on in every work conversation—but especially when communicating with executives—make your ideal end-result known. By shooting for what you think will be most beneficial, you’ll be more likely to land a palatable compromise. 

Step ten: Document and follow-up 

Once you’ve had a chance to communicate to the executive team, it’s time to take action. End your meeting with a series of tasks or a plan to enable and pay for an agreed-upon solution. If it doesn’t, make sure you have a clear plan to follow up later at a pre-discussed time.

Don't leave the meeting with no notes and no plans; this could leave your initiative forgotten and replaced by of-the-moment projects or worse, tabled without a leader. Set expectations and a course for completion right away. 

Don’t approach an important c-suite conversation, or any big workplace moment, out of fear. Your colleagues and supervisors are just like you. They care about working hard, helping their company, and going home to enjoy the rest of their lives.

On the one hand, conversations about workplace culture and job satisfaction hold the potential for a grand global impact. However, they’re also just blips on the radar of what we’re on this planet to do. By aiming to improve the culture in your workplace, you’re already doing more good than harm. The chance to see those ideas through will only further your feelings of accomplishment and reward. Enter into big workplace conversations with the confidence that you’ll make a generous impact on others. Let that confidence move you forward. 

🍪 If you need more tips for communicating with executives, here’s some sweet data to sink your teeth into: 

Zestful: recognize and reward your employees—minus the admin work.

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