10/10/19

Learn more about me here or subscribe to my newsletter here

You’ve just gotten that fancy job you’ve always wanted.VP of Eng/CRO/CPO/Head of Partnerships/whatever. Congratulations! But what do you actually do?

It often goes like this: it’s day one and you’re pumped. You have that fancy office/conf room! But as you go through meetings, your mood changes. You find that the organization is large and complex. Multiple teams and leads are vying for your attention and you can’t even keep their names straight. You’re are also detecting whiffs of trouble: projects in trouble and people who don’t like each other. A sister organization seems to be eyeing your turf. Your CEO checks in with you at the end of the day – “How are things? All good? Super excited you’re here.”. You nervously type out a “All good!” but you’re secretly worried whether you’ll survive your first three months.

Here’s a quick playbook I’ve compiled over the years on how to make the most of your first month. A lot of this is from personal experience and advice from leaders who have done this well.

First, relax! Every senior leader I’ve met has been through a similar experience when they’ve been promoted into a new role. These jobs are not easy and every single person struggles with impostor syndrome.

Second, meet everyone. Spend your first two weeks doing only 1:1 meetings and being a quiet observer in team meetings. In every meeting, cover these three topics and do as less talking as possible:

• understand that person and how they fit into the org
• three things they feel are going well and three that are not going well/need fixing
• At the very end of the meeting, ask for a couple of names for people you should meet

When you walk out of the 1:1, write up what you heard and set up meetings with the people they suggested, even if they’re outside your org.

You’ll quickly build a mental map of common themes that emerge. Project X and Y which seem to be in trouble. Person Z who everyone thinks is awesome but is just some junior data scientist in title and should probably be promoted. Compensation issues. Space issues. Within two weeks you should have a list of three things the org needs to change and three things the org needs to double down on/accelerate.

You’re also laying the ground work for relationships and information flow across the org which will be critical later on where the same people may not be as open with you as they are with a new person.

Third, make obvious people changes quickly.

Within the first few weeks, it should be apparent which parts of your team are working and which aren’t. If you need to make an obvious change and ask someone to leave or change their role, it’s better to do it early and quickly. You’ll find people expect you to do this with your fresh slate than having to do it eight months later.

This can feel very hard. You have barely gotten started and you may not even know the other person well. However, you’ll always find that these situations are obvious and the org is almost expecting you to do it (and will judge your standards if you don’t).

Fourth, build key relationships.

There are three sets of key relationships you’ll need and in the first few weeks, spend time on all of these: Your direct reports, your peers and your manager. Your directs come first – they rely on you for their career progression and are your biggest responsibility. Take them to dinner, have coffee with them. Get to know them as people and not just in the confines of their role.

The most important however is your boss: the CEO or someone reporting to him/her usually. Check in with them at all times. Pass on your observations and get theirs in return. Calibrate whether this resonates with them and more importantly, get to alignment on what they think success in your job looks like. Ideally you’re chatting every few days. Most new exec failures are because there’s no early alignment.

Fifth, pick a crisis/early win

I can’t emphasize this enough. One of the most crucial things for new leaders is having an early “win” where the team sees you roll up your sleeves and in action. This could mean any number of things – close that sale yourself, handle that incoming press/PR kerfuffle, personally get involved in that site outage. Whatever it is, it is key that people get to see you engage – your style, how you actually do the work and add value.

I’ve seen many senior execs hope for a good crisis where they can help the team. The easiest thing to do IMO is pick a quick/small project (not something that will take months) where you can have a visible win/outcome and justify your role as opposed to being just another layer of management.

In many cases, I’ve seen people form their impression of leaders for years based on this first impression.

Don’t mess it up.

Sixth, communicate.

Every single week, write out an update to your entire org on the people you’ve met and some high level observations. Write about yourself and your journey. People want to hear from their leaders and you’ll be surprised how little they know of what you actually do all day. Writing is by far the best way to get them to know you.

The key here is consistency. Send it to the same google group/alias at the same time of week with the same structure.

Finally, at the end of the month, write up a document on everything you observed from step two and send it to the org along with a few themes you want to focus on. This can feel uncomfortable – most execs aren’t used to being transparent so broadly. However, there’s real value here. The org gets to see how you work transparently but also have a mirror shined back on them from an unbiased source. I often find these docs are valuable years after the fact and good ones are the key to changing org behavior and culture.

And…that’s it! These can sound trivial but you’ll be surprised at how repeatable and applicable this playbook is across job types and industries. Remember – these jobs are hard but you’ve earned it for a reason. Trust yourself, have fun. And send me a note on how it goes!

There are many people who have given me advice on this over the years but in particular I want to thank: Boz, Adam Bain and Gokul Rajaram. The book “First 90 Days” has also been a huge help