How to Build Trust With Your Exec
Every operator knows that building a relationship with your exec based on the foundation of trust is an absolute prerequisite for success. But not everyone fully groks how important it is.
Put yourself in your exec’s shoes for a second. First, they have no idea who you are. They have heard amazing things about you, and believe you might be able to help them 10x their output and make their lives 100x better. But that’s about it.
Now, to onboard, they have to give you complete, unfettered access to everything about them - all to someone they just met! In any other context, forking over every piece of information about you would be considered one of the biggest trust falls in human history.
After all, could you imagine meeting a “friend of a friend,” and entrusting them with every piece of information about you, from the passwords to all your personal accounts, to your banking information, and even identity information like your social security number?
That’s what your exec is doing here.
Please do not take this lightly.
Your exec is likely someone who feels a real amount of fear handing everything over.
Please also do not take it personally. Anyone would feel this fear. It is a rational fear. Your job, therefore, is to give them every reason to trust you.
Here’s how.
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Do what you say you’re going to do
The best way to build trust is not only with time, but with consistency of keeping your word and commitment.
In short, you must do the things you say you are going to do.
Each time you don’t do what you say you’re going to do, you get negative trust points.
When you aren’t able to meet a promise or commitment but you update them, your trust stays neutral (but can turn into negative trust points if this happens too often. To solve this, don’t ever promise more than you can actually accomplish!)
And each time you do what you say you’re going to do, you prove a little more that the exec can believe you and your words.
BIG TAKEAWAYS
- Be lucid on what you can actually accomplish in a given timespan. Don’t overpromise. Be willing to say, “Here is how much I can do by X date.” Stick to it.
- If you’re off track, inform as soon as possible. The next best thing to delivering on-time is informing your exec and clarifying what you’re doing to rectify the situation (see below, under the section Radical Ownership of Responsibilities.)
- Give proactive updates as often as reasonable, and definitely close the loop when you finish a task to win trust points. (See: Definition of Done: Closing the Loop)
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Be certain in your actions
Another major thing any person looks for in whether they can trust you or not is how certain you are of your actions and decisions.
For every ops person I meet, the first piece of information I give them when it comes to communication is: be aware of how you carry yourself in conversation with your exec.
Many ops people err on the side of caution: after all, our work requires thoroughness and meticulousness, and we tend to downplay our own abilities to problem solve and think deeply.
However, while thoroughness and meticulousness are absolute necessities of the job, so is confidence that you know what you’re doing.
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Imagine for a second that you’re at the doctor’s office for a routine lab test. Here are two scenarios:
In the first scenario, the nurse says, “Alright, go ahead and squeeze this ball for me.” You do so, and without hesitation, she begins collecting blood. You barely feel a thing.
She then says, “And, release. You’re doing great! Just a few more seconds. You’re almost done.”
Once she’s all done, and you’ve got a happy dinosaur bandage on your arm with a cotton ball in between, you marvel at how quick and painless the process was.
Here’s the second scenario. The nurse says, “Alright, hold still. I’m going to get my needle. Ahh, are you okay? Do you have any bigger veins? I’m still getting used to drawing blood; I’m a little squeamish of needles.”
She manages to get the needle in without a pinch, but the whole time, you see that she’s hesitating and sweating profusely. Yikes.
Then, she finally bandages you up, and says, “Phew, that was great! I’m glad it panned out fine without any incidents.” Incidents?!
Which nurse would you want to see?
I know which one I’d want to see.
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Here are some things for you to try on for size.
👉 Carry yourself with certainty. Do this by being organized in how you present information to your exec. Speak slowly and eloquently, cutting out filler words like “um, like, uh, you know.”
Here’s an easy way to do this: share using this format.
- Here’s what I know about the project
- Here’s what I need clarification on in the project
- Here’s what I intend to do to get this project across the finish line. What’s your feedback for me?
Notice, I’m not asking you to bullshit your way through your projects. That’s not certainty, that’s false confidence. You should never pretend to be certain if you’re genuinely uncertain! But, rather than panicking, err on the side of curiosity.
👉 Don’t know something? Get curious and say, “I need clarification here.”
Want to check on the facts? Share what you already know and get confirmation from your exec:
“Here’s what I know about this project: X, Y, and Z.
Could you confirm this is correct?”
And write your asks for confirmation so that your exec can answer in as few words as possible. It should be as simple as them replying, “Yes,” “No,” or “Revision: _____.”
👉 Another important key is to balance how many questions you ask. Each time you make an ask, ask yourself whether you could actually declare it as a statement with feedback requested instead of as a question.
For example, instead of: “I know you asked me to buy you some coffee beans. Could you confirm the budget for this project please?”
Try instead, “I know you asked me to buy you some coffee beans, so my intention is to find some light roast whole beans around the $20 price point since you have a coffee grinder already at home. Let me know if you have any problems with this!”
Look at that example. Putting together media content and copy for your exec could be considered a project. Buying coffee beans is not a project.
In this scenario, the stakes of buying coffee beans is low enough for you to not have to ask. You can make an assumption on the price point, rather than “requesting a budget.” (If you don’t know the price point of stuff, ask ChatGPT or Bard.)
BIG TAKEAWAYS
- Speak with confidence. Eliminate filler words.
- Decide how big or small your task is. Get clarification for bigger tasks; move with speed for smaller tasks.
- Think about what you know and don’t know. State to your exec what you know. Ask for clarification from your exec for things you don’t know and can’t look up yourself or can’t make assumptions on. This proves that you are self-aware of what you know and don’t know, further instilling a relationship of trust.
- Use ChatGPT or Bard to help you with your assumptions.
- Phrase your asks to your exec so they can reply in as few words as possible: yes, no, or revision.
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Speak Like You’re the Chief of Staff to the President
(I already wrote about speaking like you’re the Chief of Staff to the President in this doc, so please refer there for what this actually means.)
BIG TAKEAWAYS
If you can speak like you’re the Chief to the President, it means you are…
- Envisioning how things will work several steps ahead
- Anticipating potential hurdles and how to solve for them
- Thinking about every step that has to be done for the work to be accomplished
- Providing everything needed to accomplish that work
- Briefing your exec on what they need to know to do an exquisite job
Embrace your inner Presidential Chief of Staff, and you will win major trust points with your exec.
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Radical Ownership of Responsibilities
Finally, you must take extreme ownership of your responsibilities.
When you’ve done good work, share that work with your exec as a means of updating them on the most recent situation.
When you’ve made mistakes:
- Own the mistake by sharing with the exec what mistake you made
- How you’re rectifying the situation with the actions you’re taking
- If it was a very serious error, say an apology (“I’m sorry, here’s how it won’t happen again” goes a really long way.)
Do this by incorporating it into your Start of Day and End of Day reports.
The success or failure of your exec’s ability to do amazing work and run faster is directly correlated with how willing you are to do all of the above with a sober mind.
This means not groveling and beating yourself up if you’ve made mistakes, because now you’re making the situation about you and your feelings, rather than about rectifying the mistakes.
The left column will cause your exec to not respect you, because they’re constantly thinking about how to make you feel better. (It’s the column I find most EAs gravitating towards.)
The right column will give you zero grace when you make mistakes, and will likely get you fired no matter how good you are. (It’s the column where I find most arrogant, insecure people live.)
And the middle column will win you extreme trust. You’re speaking clearly, you own your mistakes, and you communicate in a measured, level-headed way. (It’s where you want to be!)
BIG TAKEAWAYS
- Own your actions, the good outcomes and mistakes alike.
- Share these updates proactively in your start of day and end of day reports.
- Don’t apologize for everything. Apologize for the things that are truly big mistakes.
- Don’t grovel - groveling makes it about you, rather than the mistake you’re trying to rectify.
- Don’t be an overconfident jerk - it’s the fastest way to get you fired.
- Approach your communication in a level-headed way.
