Hacking Your First 90 Days



Question: Who is more responsible for a successful onboarding into a new role, the company or the employee?

Answer: Most successful companies today "get" the importance of accelerating the time from hire (or promotion) to impact. It's a simple equation. Employees, however, don't necessarily always do all that they should to guarantee their own success in this onboarding period - typically defined as the first 90 days.

I think this is why I am often asked how it is that I deal with constantly changing roles and moving around the world while having to successfully integrate with dramatically different environments. On the outside looking in it may appear that I have some secret formula enabling me to hack the process of adaptation to different job descriptions, managers, cultures, and companies. In truth, everything I've learned about managing career transition I first read about in The First 90 Days by Michael D. Watkins.


In his seminal bestseller, Watkins breaks down the discrete stages of matriculating through the first quarter of the journey into a new role. The key principle is that as a new employee or someone new in a function or market, you have a limited amount of time to demonstrate your value. The clock is literally clicking and under this kind of pressure lots of people crack. But there are select few who seem to know exactly what to do and prioritize the right sorts of activities within this window to build relationships, generate quick wins, and accelerate their learning curves. While some people do this intuitively, there is actually a structured way to approach your first 90 days on the job.

This is broken down into 5 key dialogues that should occur over the course of 3 months:

  • The style conversation

  • The expectations conversation

  • The situation conversation

  • The personal development conversation

  • The resources conversation

The Style and Expectations Conversation:

The first stage comes down to aligning styles and expectations with your new manager.

The key here is to assume nothing and seek to understand and to be understood.

You were chosen for this role for a reason, but don't take it for granted that your new manager automatically is going to give up the keys to the kingdom. There is still more that they don't know about you than they do and vice versa, so consider this an important ice-breaker exercise before getting too deep into the day to day work. Key information to exchange are the basic personal details such as name preferences, birthdays, siblings, hobbies and interests, inspiring figures, and key career turning points.

I always recommend having a conversation about trust builders and trust breakers because everyone has different guard rails when it comes to this crucial topic. You can broach the subject by simply asking what are the behaviors that matter most to each of you in your working relatioships. It's fairly safe to assume that the opposite behaviors will have the opposite impact on relationships. Once this is out in the open, it's usually smart to request immediate feedback should you hit or cross a guard rail inadvertently in the early days of your working relationship.

Other expectations to confirm include communication preferences (as in when to use which channel such as email, SMS, internal chat, or phone); and other more general expectations such as what does your manager expect of you functionally, as a contributing team mate, in terms of time commitment, travel, availability, and hierarchy (when do you have autonomy and when do you need to check in). Getting all this on the table as soon as possible will define your success in your new role and help you avoid any faux pas as a result of ignorance.

The Situation Conversation:

Coming into a new role can be a bit like being a detective investigating a crime scene. You need to quickly come up with a hypothesis for why and how the performance, product (s), project, or processes (or all of these) ended up in the current state and generate some ideas for what actions should be prioritized to generate some quick wins. Starting with why is the crucial concept in this stage because you truly need to get to the bottom of the situation you are facing, confront the brutal facts, and identify areas within your immediate sphere of control to act upon. You want to meet with a wide variety of stakeholders in this stage to gain context, perspective, and generate options before making any decisions.

Many a new employee is derailed by making a decision before having gained the proper context.

In this stage your manager is a key player once again because you want to validate your findings with her/him before getting down to business. For my new teammates I recommend the following analysis and presentation to be made to me within month 2:

  • Augment what you know: increase your base of current facts

  • Identify what you need to know: accelerate your learning curve

  • Assess your function situation: strategy, structure, systems, skills, and culture

Once you have alignment on the path forward, you will act with far more confidence and precision and generate value far faster than acting without understanding and insight.

The Personal Development and Resources Conversation:

During your entry into a new position, company, or role, certain aspects of the job will naturally come far easier to you than others. This might be due to previous experience, role/culture fit, your unique talents/strengths, or some combination of these parts. It's important to note which segments of your job are easy and which are posing greater difficulty and be open and vulnerable enough to discuss these with your manager at the appropriate time. I recommend within month 3 because by this time you have made some decisions, taken some actions, and gotten into some semblance of routine.

The key reflections to make pertaining to your own journey to this point are as follows:

  • What strengths, skills, knowledge, capabilities do you have in your toolbox that will definitely work?

  • What additional strengths, skills, knowledge, capabilities do you need to acquire to cover your gaps?

  • What have you done in the past that will definitely NOT work for the current situation?

Honest and transparent reflection on these areas will be the jet pack powering you beyond 90 days to deliver outstanding value in your new capacity.

Knowledge of self is truly powerful just as self-deception is truly destructive - especially in the early going.

Once you have answered these queries you know what to prioritize in terms of your development and developmental relationships such as with coaches and/or mentors. Still, there may be natural limiting factors in your department such as budget, systems, or headcount gaps that need to be addressed and this is the time to call them out as crucial to attain your full potential. Your own expectation needs to be tempered by the reality of your department and company situation, but recognizing your constraints and risks is a mature way to proceed and align with your manager on how to make progress together.

Hopefully, you can see that with these three conversations you can rapidly advance your realationship with your new manager, increase your understanding of your circumstances, and identify areas to continuously develop and improve - which should speed up your successful entry into your new role. I personally have applied this methodology for the past 14 years both as an employee and as a manager with my new team members and have enjoyed the results.

Here, please find the simple template I created to structure the onboarding process. Hope it helps you as much as it has helped me! If so, please give this blog a thumbs up and/or share with someone in your network who is starting in a new role!

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