Congratulations! You’ve signed your offer and you’re a newly minted Chief of Staff.

But you’re still anxious. What if my colleagues don’t like me? What if they don’t trust me? What if I fail on the job?

Onboarding is always an awkward time for anyone. This is compounded by the fact that you are now in a super-highly scrutinized position.

So how do you quickly build trust and relationships? How do you arrive like the newest cast member of Friends? How do you fit right in?

I recently explored these questions in a 1:1 coaching session with a fresh-faced Series C startup Chief of Staff. This newsletter is an edited and condensed version of our conversation.

Now, let’s get into the specifics below of how to maximize your first 30 days to win over new friends and become an effective Chief of Staff.

✅ Create a likable & presentable “first-impressions” persona

Be nice, personable, and non-controversial. You don’t want to create any controversy or drama. Do NOT do anything the Roy family would do on Succession. Pay careful attention to your attire. Figure out what the standard of dress is and find a comfortable outfit that matches the level of formality of your new company.

Create your digital persona. Update your Zoom background & lighting. Since you will likely be meeting new remote team members make sure that you pay careful attention to your backdrop. Also, update your LinkedIn profile. Your new team members are definitely checking you out on LinkedIn before and after you meet with them. Make sure your profile picture, tagline and about me section are all portraying the exact narrative that you wish to convey. Check out my recent newsletter on how to do this.

✅ Find an internal company guide to get up to speed quickly

Ask your boss for a guide in the organization. Identify a strategy or operations person and get their buy-in. Request all strategy, operations, and systems docs from them so you can get up to speed quickly. Use them as a reference and sounding board as you complete your onboarding.

✅ Create a digital personal user guide

Define how you best like to work and collaborate with others. Put your guide in your email signature or Slack profile. Tell people about it and why you are sharing it. Why is this important? You get to trust faster and establish working relationships faster. Use my Typeform template here to jumpstart writing your guide. If you’re curious to see an example, here’s mine. Reference this document on your listening tour (see section below).

✅ Mindmeld with your boss

Spend a lot of time shadowing your boss. In-person to start is best. Understand their working style and figure out the way they make decisions. See how they interact with their reports. Review their emails and other communications to see the way they write. Figure out what is priority and what is not. Remember, you’re doing this to become their proxy faster and then save them time.

✅ Deliver value immediately

Move into execution mode. Look at the bottom 20% priority tasks on your boss’ list. Begin with small, low-stakes tasks. Develop small wins to start. Later on, you will grow these continuous small tasks into bigger projects. Initial Tasks could be: review a doc, prep for a meeting. Create a weekly email recap of your wins to send to your boss to surface your value.

✅ Complete the Zone of Genius exercise

Create a skill will matrix. Define what you are good at and what you like to do. That’s your Zone of Genius. Share this with your boss and ask if you can do the same exercise with them. Guide them through this using my Figma template and LinkedIn post. Make a joint commitment to helping you and your boss stay in your respective Zones of Genius, while delegating other tasks as much as possible to the rest of your team.

✅ Get multi-level sponsorship from your boss

Create an internal communications plan that communicates your role. Get buy-in from your boss that to be successful, you need multi-level sponsorship at the company. Ghostwrite the communications and have your boss approve. Create a mix of Slack, email, in-person, weekly and all-hands communications. Topics include, what’s a Chief of Staff, what are the benefits, the scope of your role, your current mandate, etc.

Execute the communications plan. A mix of formal and informal sponsorship communications is best executed over multiple months. Take note of people’s reactions to the communications.

✅ Establish a world-class executive enablement team

Get to know the EA on a deeply personal level. If there is an Executive Assistant or Office Manager, they will become your new best friend. Ask them what’s their career path, what are their values?

Ask them for company information. Ask them about the history of the company. Ask them how things work at your company. Get coaching from them on the background of key stakeholders.

Sell your vision to them. You want to create a world-class partnership to help everyone thrive at your company, including the executive team, management and employees. Get their buy-in.

Define your new executive enablement system. Create a working doc of your roles/responsibilities. Define what’s in scope for you and what’s in scope for them. Define the interaction model between you two, ie a triage system for incoming requests. Figure out what tools you will be using.

Create space for them to thrive. Give them a pathway to continuously develop in their career. This could be that they could take on more scope or responsibilities. Get ahead of any personnel issues so they don’t feel threatened by you on the job.

✅ Conduct a thoughtful listening company tour

Create a list of key stakeholders that you should meet. Ask your boss for a list of people that you should meet and in what order.

Conduct conversations. Ask them… what are your goals? What are the areas that you need support? Where are you trying to go in your career? What’s your life story? Figure out what drives them. Be vulnerable and share your own story. Acknowledge any issues that they might be facing and make an internal commitment to helping them solve them in the future.

Reflect on what you heard. Create a stakeholder map for yourself. Take notes on their style, warmth & assertiveness. Add a RAG status = strength of your relationship. Share your insights with your boss.

And that’s my Chief of Staff Onboarding teardown.

If you follow these tips, you will onboard as a Chief of Staff and create trusted relationships from the jump. You’ll become effective at your job faster. And you will smoothly insert yourself into your company just like a new cast member of Friends. Time to go fountain hopping!

Need help onboarding to your new role?

We provide advisory services and 1:1 coaching for both CEOs/leaders and Chiefs of Staff to make onboarding a breeze.

Our team of expert advisors provides dedicated training, development, and coaching to ensure that your Chief of Staff-Boss relationship is working smoothly and that you, the new Chief of Staff, are up to speed in your role as quickly as possible.

We also provide dedicated coaching for founders / CEOs that have never had a Chief of Staff before, helping them to get the most value out of their new 2nd in command.

Reply to this email if you’re interested in learning more or check out our website for more information.

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