How to Win Executive Trust in Your First 90 Days

April 23, 2020
Guest Post
Friend of Drafted

Jen Paxton is the VP of People and Talent at Privy. Jen is a leader in the PeopleOps space and has partnered with Drafted to release a 5-part series for PeopleOps leaders that are just starting out or at the frontlines of a hypergrowth startup.

You are just getting settled into your new role, you have so many things that you want to accomplish at your startup and you have determined the program and/or software that you want to start with first. You know deep down that this program/software is going to help many people in the company and support the company’s overall goals. 

Now is the time to get buy-in from your CEO and other executives at the company. But how do you do it? 

Getting buy-in is like baking a pie. Set the foundation “crust” with data - if you don’t have a sturdy foundation the whole “pie” will crumble. Mix the filling with middle manager desire or buy-in - you need to prove that people need this, get allies to rally with you for the cause. Sprinkle ROI on top for the business - prove that doing X will provide Y, that’s when you have your ROI. 

I must apologize for the pie analogy, being cooped up under quarantine has given me more time to bake, so pie is top of mind for me.  


Building a Relationship with Your CEO 

I would argue that the relationship between your PeopleOps leader and CEO is one of the most crucial to get right. Your partnership will build the business for good or bad, if you are not on the same page, that’s when things can go wrong. 

Like any relationship establishing trust is key to a strong partnership. You want to show that you are adding value and making an impact (I mean that’s why they hired you after all, right?).  

Your CEO didn’t hire a PeopleOps leader to take notes or be a “yesman.” They hired you because you have ideas and plans on how to help them grow their culture and business. They hired you to push them and other execs to grow as leaders and be the voice of the employees when something needs to change or improve. 

PeopleOps is about supporting our people as well as helping the company to achieve its business objectives. In the back of your head when you are making any decision for the company are you asking yourself, “Am I building this for the people and the business?”  

As I have gone through my career I have had to strike the balance between serving the people and serving the business. Mostly they are one and the same, but sometimes they can diverge.  

You need to have open and honest communication with your CEO. You are going to have differing opinions on occasion and that is ok. They did hire you to speak your mind and help them with any of their “blindsides.” 

You need to spend your first few weeks earning trust. Do what you say that you are going to do, don’t over-promise or make excuses if you don’t get something done. This starts but having an open conversation on expectations. 

Be helpful and find ways for you to support your CEO and leadership teams, some quick wins can lead to bigger ones. 

Really Digging In 

Every team is going to have gaps and each leader has goals to fill those gaps. It’s important to understand that every executive you work with is going to be different and have different goals. 

In the first few weeks, really the first few months you get to play detective and uncover all of the gaps that you can on a team. After that, you can start to build a plan to fill some of those gaps. When working with a leader for the first time, you will need to show you can personally add value to their team and support the team as a leader. 

When I start out at a company I think my favorite phrase becomes “can I help you with x?” I love to ask this because not only does it help the leader I’m asking with something, it also starts to build trust that I am here to support them. Then over time there’s a switch that happens and instead of me saying “can I help you” they are coming to me to say “Jen, can you help me with x?” 

Sharing Your Data 

As a PeopleOps leader, you are spending time with other executives collecting data about what they want and what they’re looking for. Over my career, I have learned how to leverage data in a way that is clear and also persuasive. I have bi-weekly conversations with most of our executives to keep a pulse on how their teams are feeling. 

Once you collect the data you will want to create a cycle of feedback where you share this data with your CEO. I treat these meetings as a way for me to be an extension of the CEO’s ear. I take notes during each session and find themes in this data to bubble up to my CEO. In some instances, I’m coaching the leader to chat with our CEO about this topic first then reaffirming them in my 1-on-1.

Winning Executive Buy-In 

There will come a time when you will need to get buy-in for a new tool or program that you want to implement. Start by collecting data from various teams in the company to get a temperature read on whether or not this is something they could see adding value to their current process. 

I tend to float ideas in my 1-on-1 sessions with leaders first to socialize the idea and get their level of interest. This is a good low-risk way to get opinions before bringing it to the larger group. This also helps to overcome objectives early on before you have spent too much time crafting the plan or program. 


Building executive trust won’t happen overnight. It takes time to find all the gaps you can fill. Spend your time collecting your data when talking to all of the executives at your company within your first couple of months. Use this data to build your foundation in winning that executive trust and stay focused on creating a strong partnership with your CEO. 


This blog post is the second part of a five-part series. In series three of How to be a PeopleOps Leader at a Growth Startup, Jen Paxton will share How to build a long term vision for employer brand and culture at your company. In case you missed it, check out part one -  Setting Up for Success


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