How to Make the Most of Your First 100 Days as a Tech Executive

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How to Make the Most of Your First 100 Days as a Tech Executive
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Table of Contents
  • Introducing expert tech executive consultant Aviv Ben-Yosef
  • Why your first 100 days as a tech executive matter
    • 1. It’s the best window you have to change things
    • 2. You’re more objective in the first few months
    • 3. The first 100 days define your impact in the organization
  • 4 steps for navigating your first 100 days as a tech executive successfully
    • Step #1: Manage your time
    • Step #2: Triage all requests and tasks
    • Step #3: Make critical personnel decisions
    • Step #4: Introduce initiatives
  • Final thoughts on making the most out of your first 100 days as a tech executive

Companies often invest time and resources in their onboarding processes to give new hires a positive impression and get them settled in faster. But as a newly hired or promoted tech executive, you probably wouldn’t be onboarded if you’re joining a startup.

Still, you need to learn everything about the company, its product or technology, upcoming strategic decisions, and weak points to do your job right.

If you get into your new role reactively, attending to the requests and problems as they hit your mailbox, you may quickly get overwhelmed and miss the opportunity to make an impact as a tech executive.

How, then, can you maximize your first 100 days as a tech executive despite everything you have to do and the lack of proper onboarding?

If that’s what you’re asking yourself, then you’re in luck. During one of our recent Tech Leaders Hub sessions, we spoke with expert consultant Aviv Ben-Yosef, who is passionate about helping executives, managers, and engineers realize their full potential and build high-performing teams.

Keep reading this article to tap into Aviv’s insights and learn how to strategically navigate your early days as a tech executive!

Introducing expert tech executive consultant Aviv Ben-Yosef

Aviv has been coding since he was eight years old, so it’s no surprise that he also had an interesting career. He served in the Israeli Army and worked as a software engineer in IBM and some startups.

After leaving full-time employment, Aviv transitioned to an independent consultant, working with startups, small businesses, and Fortune 500 companies across Israel, the United States of America, and Europe.

After a few years of helping his clients succeed, he decided to teach them how to succeed, and now focuses on advisory and coaching services for Chief Technical Officers, Vice Presidents of Engineering, Chief Executive Officers, and other engineers. He helps them increase their impact-per-engineer, escape being treated as Jira resolution machines, and explore their potential to the fullest.

In 2020, Aviv published his first book, The Tech Executive Operating System, which has received amazing feedback from tech professionals globally. He also shares regular tips to help tech leaders build high-performing, autonomous teams in his weekly six-minute podcast, called The Tech Exec Podcast.

Aviv finds the impact of his work on people’s lives and companies that are better off, successfully exit, become unicorns, or go public more fulfilling than the joy he derives from coding. He hopes to help more companies become successful through self-materialization.

This article covers our discussion with Aviv extensively. However, if you’d rather watch the live session, here’s the link to the full recording of the live session.


Why your first 100 days as a tech executive matter

One hundred days may seem like a short period to do much in a new role, but it actually isn’t. The first 100 days are crucial to your successful tech executive tenure, and here are some reasons why:

1. It’s the best window you have to change things

According to Aviv, “There is always a window of malleability that comes with transitioning to a new role, which is a limited time you can get credit for making changes. People anticipate that things will change when a new sheriff is in town.”

However, this window of malleability is pretty slim—roughly a quarter of a year. After this period, people assume it’s business as usual. If you don’t seize this time to make changes, you’ll have missed your best shot, and it’s often harder to make such changes later.

2. You’re more objective in the first few months

As a newly appointed executive, your biggest advantage is what Aviv describes as your beginner’s perspective, which is your perception of the company before you become acquainted with its processes, product, people, values, culture, and everything specific to the organization. If you don’t take note of the company’s weak points and idiosyncrasies, you’ll miss out on key insights.

3. The first 100 days define your impact in the organization

According to Aviv, “Tech leaders are often great at the technical requirements of their role, but struggle with the leadership aspect and end up as glorified managers instead of executives.” You have your first 100 days to avoid falling into this trap.

Hence, it would be best to build rapport with colleagues, learn about the company’s visions or plans, and strategically position yourself to get a seat at the decision-making table within the first 100 days.

4 steps for navigating your first 100 days as a tech executive successfully

Just knowing why the first 100 days matter is not enough to help you avoid getting caught up in the chaos and create impact. You still need to be tactical to not get sucked up in day-to-day operations and create impact instead.

Aviv shared with us his four practical steps you can use to navigate your first 100 days as a tech executive successfully.

Step #1: Manage your time

Time is the most important asset at your disposal during your first 100 days. It’s easy to lose track of it with so much to do so quickly.

As a tech executive, you’ll generally spend a lot of time interacting with people. In your first 100 days, it’s especially important to spend time getting to know the stakeholders to gain full understanding of the company’s product as well as the business, its customers, and competitors—not to mention the company’s five-year strategic vision.

Aviv recommends alloting an average of two hours daily in the first 100 days to learn about the company and build relationships with people.

Who should you talk to?

There is no hard-and-fast rule, but Aviv recommends talking to the following people:

  • The brains behind the product: Talk to the Head of Product, Head of UX, and generally anyone responsible for making the product happen.
  • Your line manager: Aviv also recommends talking to whoever you report to in order to learn about the fears and risks of your organization in the near future and gain access to the roadmap and strategy.
  • Other executives: Next, talk with anyone who is a senior leader, such as the Head of Customer Success, Head of Marketing, and Head of Growth.
  • Other employees: You should also have an introductory meeting with everyone, as you may have to work with them occasionally as a tech executive, and you can find out what’s going well for them in the organization and what isn’t. It would help if you also did this routinely. In a small startup, you can talk to everyone once in a while, and in larger companies, directors, managers, and from time to time, everyone else.
  • Customers: Finally, you need to understand how your customers act, think, and use your product. Talk to your customers, too—not necessarily in the first 100 days, but in the first few months.
Tips for building rapport with your stakeholders

Talking to your colleagues can be quite a task, since you’re trying to get relevant information from different people, and having these conversations is a great starting point for building a great team instead of a bunch of executives working in silos. Here are two pieces of advice from Aviv to help you navigate these conversations:

  • When talking to counterparts, ask about their background. If you understand their path, you will better understand their thinking and what they want to achieve. Also, Aviv recommends finding out the most critical thing the organization can do for them and the biggest risk to be averted. If it’s too big and not immediate, write it down, think about it, and see if you can help later. 
  • When talking with subordinates, ask them to introduce themselves and inquire about the unique thing in their current role compared to the rest of their career. Use more open-ended questions to keep the conversation going.
Step #2: Triage all requests and tasks

Triaging requests and tasks instead of working on them linearly prevents you from getting overwhelmed. You can add requests and tasks to a to-do list using the Notepad, Google Docs, or a sophisticated task management system like ClickUp to organize requests and monitor your commitments, the promises you made, and the promises you received, so that nothing falls through the cracks.

Afterward, take some time to triage what’s on your desk, or in Aviv’s words, clear the fog of war. Next, you need to come up with a plan, which should be delivered within the first two months into your role. Sooner will be premature, and later will miss the window of malleability.

How to triage requests and tasks

First, you’ll need to quickly put out some fire no matter how unreactive you try to be, so you need to prioritize urgent requests. After you figure out the tasks to be handled right away, find out if you need to execute them personally.

It may turn out that you’re not the right person to handle all requests and will need to delegate to someone else or a different organization. If something isn’t your direct responsibility or doesn’t need to be handled immediately, keep it on your triage list.

Secondly, review all requests in batches. Some may no longer be relevant, in which case you can safely delete them. You may also notice a theme, need more information for some requests, or need to have a follow-up talk with whoever is responsible for such a request.

How to create a plan

Your plan does not need to be a complex or detailed document. It could be a single Google Doc page with summarized notes. More importantly, your plan should feature the following:

  • Solutions to burning issues: In Aviv’s words, “Create a list of fires you want to put out and a plan for containing the fires so it doesn’t get to a point where you need to evacuate.”
  • Issues requiring further investigation: Aviv also recommends including a list of questions you want to dig deeper into, because you can’t figure out everything you need to know within the first 100 days. There may be features or people you never got to see.
  • Solutions to the company’s weak points: You should also add solutions to the company’s weak points, such as changing the company’s business model or organization structure, as well as recommending multiplying something working above the bar in your organization.
Step #3: Make critical personnel decisions

Within the first three months, you may need to make some personnel changes in your company, which Aviv refers to as chart debugging. For instance, your company may have too many small teams with managerial overhead or large teams with an overworked manager. Should that happen, you’ll need to figure out a hiring plan to fix these issues.

You may also realize that the company has a high attrition ratio and need to figure out the reasons for that high attrition rate, or make plans to hire more people because you realize the others will leave either way.

Making these personnel decisions is usually not an easy task for most tech executives. As Aviv puts it, “Tech decisions are a lot easier, but personnel decisions are tough decisions and tough conversations that need to be handled sensitively.”

Sometimes, organizational problems can only be fixed by restructuring roles within the company, which may be difficult for the staff and executives. It’s advisable to talk to the individuals affected when making such decisions. You can also consult a trusted advisor to help you figure out these personnel decisions.

Step #4: Introduce initiatives

A major part of your role as a tech executive will be introducing initiatives to help your organization achieve its strategic objectives, and the first 100 days is enough time to start rolling out these initiatives. Hence, it’s advisable to figure out the big initiatives you’d like to introduce in your organization as soon as possible.

These initiatives can range from determining the projects you’ll be leading to moving your team from a featured one to a product-empowered one. How you introduce these initiatives matters just as much as the initiatives themselves.

Therefore, it’s important to present your initiatives to the right people. According to Aviv, “If there’s something tech executives often get wrong, it’s presenting their initiatives to too many people at the same time.”

Presenting your initiatives to relevant heads of departments and tech executives whose activities may be affected by these initiatives is a more effective method. In addition, Aviv also recommends sharing these initiatives with managers and relevant colleagues to get their input.

Similarly, it may be best to announce initiatives in bits depending on the relevance of each initiative at the time. However, some people prefer to roll them all out at once. Whatever the case may be for you, make sure that you leverage your good rapport with colleagues and consider the company’s strengths and weaknesses when introducing these initiatives.

Final thoughts on making the most out of your first 100 days as a tech executive

Your first 100 days as a tech executive could be the defining point for the rest of your executive tenure. There will be a lot to do with little or no guidance, and you’ll also have to go fishing for information.

That’s why it’s best to take a breath and navigate the early days’ chaos by maintaining a vision over the horizon and not getting swept up by all the endless meetings that pop up on your calendar. Luckily, the tips we’ve shared here should be enough to serve you as a roadmap for successfully navigating your first 100 days as a tech executive.

Thank you for reading this article. We also recommend you read the following helpful guides and resources for tech leaders on our website:

Subscribe to our Tech Leaders Hub newsletter for more content just like this. Also, if you need to restructure your team by quickly extending its capacity, feel free to check out our team extension services, among many others.

And if there’s anything else we can assist you with, simply reach out to us directly and we’ll get back to you in no time!

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