The First 100 (remote) Days

Given today’s new remote environment, onboarding and ramping up to a new role may be more challenging (and exciting!) than before. As work communication today is purely enabled by technological enterprise tools – Zoom, Slack, Facebook Messenger, Microsoft Teams – we may face different challenges vs the pre-remote world.

To author this – I collaborated with Meet Dave, who remotely onboarded and transitioned to a leadership role at Bell Canada as a Senior Manager of Product Marketing. Together with some inspiration from the classic “The First 90 Days” – Michael Watkins, we set out to brainstorm and define some universal onboarding best practices. We wrote this piece to provide general principles for the folks out there going into a new opportunity.

First impressions matter, and the initial experience for new candidates has quantifiable impact on job satisfaction and even employee retention rates. Part of the equation is the onboarding experience from the employer’s side – but it is equally, if not more important for the employee to proactively prepare for the transition as well.

Drawing some inspiration from politics – it is standard practice for US presidential candidates to create a 100-day action plan to present their priorities going into the role. At my previous company, analysts seeking a leadership role are required to build a 100-day plan to share with the senior leadership team as part of their evaluation process. It is a tried-and-tested rule to ensure productivity in the first three months, and beyond.

This framework is meant to be less prescriptive and more thought-provoking; it serves as a guideline of topics and ideas to think about during your onboarding journey.

Below are six themes I’d urge you to consider and reflect on during your first 100 days.

1. Close off the previous chapter

As you transition to a new role, team, or company, it’s essential to receive (and share) honest feedback on your previous post. Set up thorough 360-degree feedback sessions with your leader, team members, and cross-functional stakeholders to understand the impact you had and value you delivered.

Some questions you may want to ask:

  • What were some of my greatest successes in the role?
  • What did you like the most about working with me?
  • What are some areas that I need to improve on?
  • What are some opportunities I may have missed?

Additionally, everyone adapts differently to a remote work environment – take note of how the shift to remote has positively (or negatively) impacted productivity and the work experience. It’s also worth reaching out to your mentors to discuss your transition, but also to get their feedback and thoughts on your path ahead.

Ultimately, the goal is to collect insights, data points, and feedback for you to be cognizant of your working-self and to continue to develop your brand so that you’re confident going into your new role and have an awareness of your strengths, weaknesses, and traits.

2. Visualize and prepare for the transition 

Take into account the feedback and inputs from your previous coworkers and mentors to create a holistic view of who you are (and who you want to be).

Picture yourself in your new role

How will you introduce yourself? How will you tell your story? What are your experiences, skills, and qualities that make you unique? What are your values?

Additionally, how will you communicate this effectively in a remote environment?

Plan for anticipated challenges

Some challenges specific to remote onboarding could be:

  • Limited access to resources
  • Communication barriers due to technological issues
  • High level of ambiguity; lack of direction
  • Distractions in the home environment
  • Difficulties building or learning team culture

To avoid these risks, you may want to develop a mitigation plan. For example:

  • Build out your pool of resources beforehand. Compile external resources such as industry blogs, financial reports, cross-industry SMEs, or case studies for reference in the future.
  • Create workflows for the worst-case technology issue scenarios. Perhaps you can automate an email to your meeting stakeholders with an external conference bridge if the Zoom isn’t working. Or, have a a file converter readily available in the scenario that pdfs are struggling to open. Just a few examples.
  • Invest in your ideal work-from-home environment. Upgrade your headphones with white-noise cancellation technology. Order an accurate microphone to eliminate background noise. Get a standing desk to fix your posture. Set rules around the house to support your productivity.

Have these thought-out and activated prior, so that on Day 1 – you’re good to go.

3. Create a comprehensive learning plan

Build a framework for absorbing technical knowledge that considers: at a macro level, the industry and company – and at a micro level, the team and role.

Industry & Company knowledge

Put in the time to research, brainstorm and critically think about the operating environment of a company. Even if you’re just transferring to another team or role internally, it may be useful to revisit this exercise to get an awareness of where the business is today (and where it’s headed tomorrow). There are an abundance of frameworks to learn about an industry and company. Taking us back to Marketing 101 – some classic examples are: 5Cs, SWOT, 4Ps, and Porter’s 5 Forces. Personally – I find the 5Cs framework most thorough and useful.

  • Company – How does your company serve its customers? What’s the history of your company? What products are offered? What’s your company mission and brand about?
  • Collaborators – Who are the stakeholders in the value chain? What industries and companies enable your company to be most productive and profitable?
  • Customers – Who does your company serve? Who are the key user groups? What do the users think of your product?
  • Competitors – How intense is the competitive rivalry? Which competitors exist in the space and how do their value propositions differ?
  • Climate – What stage of growth is the industry in? What role does regulation and government play in industry?

Leverage a mix of both internal and external resources. It’ll also be useful to keep track of all the new terminology you come across.

Team and Role-related knowledge

The PPT (People, Process, Technology) framework is practical for learning about how a specific team operates. Again, there are many different models to use – I find this one the most simple and coherent.

  • People – Your team’s stakeholders and resources.
  • Process – The workflows involving people and technology to achieve your team’s goals.
  • Technology – Tools and technology that will enable your team to be successful.

Additionally, consider past successes and failures. What projects have been successful in the past? On the contrary, what has your team attempted in the past, without success, and what were the lessons learnt?

Ask a lot of questions and observe, observe, observe. How do your colleagues interact with each other? How do they productively debate? What are the key tenets of the team and company culture?

4. Set expectations with your leader

Drive early discussions with your leaders to start building trust and setting expectations. Given the lack of face-to-face engagement, it’s key to be over-communicative in a remote setting.

Michael D. Watkins presents a useful framework of ‘five conversations’ to have with your leader:

  1. Situational Diagnosis – How does your leader perceive the business situation? What are their priorities? What are the opportunities and threats today? Tomorrow?
  2. Expectations – Clarify what you’re expected to achieve in the short, med, and long term and set goals, milestones, and metrics to track your progress.
  3. Style – What communication and working style is preferred? What is the suggested cadence of check-in points? When are you expected to be online?
  4. Resources – What resources will you need to be successful? Additionally, what resources is the organization lacking today, and how can you solve this?
  5. Personal Development – What is your 3-5-10 year plan for career development and how can your leader support you in reaching your goals?

5. Create an action plan

Introduce and promote yourself

As an individual contributor, build rapport and familiarize yourself with the organization by scheduling 1:1s with team members, cross-functional colleagues, and other leaders in the company. Going back to a few of the earlier points – have a strong introduction, share your background, and promote how you can contribute value to their portfolio and current challenges.

As a people manager, it’s important to have a similar approach with your direct reports. Ask questions and learn about their portfolios, personal growth objectives, and preferred leadership style. To drive strong performance as a new leader, your goal is to ensure that your direct reports buy-in to your vision and trust that you’ll act in their best interest. Imprint a results-oriented culture of winning and acknowledge that your success as a leader is a direct by-product of their accomplishments.

Build a roadmap of low-hanging fruit vs long-term projects

Achieve early wins. After having some familiarity of the portfolio and the business priorities, define a roadmap and find areas where you can make an immediate impact. Quick process improvements and workflow efficiencies are common areas; if you’re able to make a process faster, cheaper, or better – whether it’s a spreadsheet macro or marketing automation – any time savings or incremental benefit will show that you have a proactive mindset.

For direct reports, use the onboarding period to analyze their portfolio against broader strategic goals – are their current projects and priorities aligned to the key metrics and KPIs of the team & organization? Through this, you may also discover an opportunity to re-distribute priorities across the team to best cater to each individual’s unique skill-set and development objectives.

Track your success metrics and seek feedback early on

Following discussions on expectations, you should have some clarity on what is expected from you in terms of duties and responsibilities, and ultimately – business results.

Curate a ‘personal scorecard’ and select a few metrics to track your performance that make sense given the scenario. In the learning phase, you may want to accomplish X coffee chats, or learn X tools. As you’re further into the role, you may consider setting a target of X hours saved with automation or process improvements on your workflows. If you have direct influence on revenue, think beyond sales targets to sales productivity metrics as well.

6. Maintain the momentum

Lastly, continue the momentum. Opening with an effective onboarding plan (and executing it well) will serve as a springboard into your new role. Continue to integrate principles across the themes of learning, growth, communication, and execution throughout your tenure. Keep seeking feedback to incorporate into your career growth and development plan, and proactively action on these areas.

Feel free to reach out with any thoughts, ideas, or questions!

Andrew is currently an Operations & Enablement Lead at Facebook New York, focused on building and scaling new initiatives to support the performance of global sales teams. Previously Andrew was at Bell within corporate strategy, marketing, and operations, working on providing a best-in-class customer experience. Andrew is incredibly passionate about the areas of innovation, growth, learning, and performance psychology—Andrew writes about these topics on LinkedIn and Medium. Outside work, Andrew trains mixed martial arts competitively (Brazilian Jujitsu & Kickboxing) and loves to play chess.

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