Onboarding on Talkdesk with a 90-day Plan

Tiago Costa
Talkdesk Engineering
7 min readNov 21, 2022

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Man onboarding a plane by Erwan Hesry on Unsplash

Remember the last time that you accepted a new job offer?

The excitement of a new challenge, a unique opportunity with new challenges, new people, and new culture. It almost feels like embarking on exploring the sea as our ancestors did.

However, changing jobs comes with some associated risks. From my experience, making or not making the correct impressions in your first days can either set you up for success or have you face a dreadful path where you need to fight to achieve success. I have my fair share of experience meeting the latter option, which is not fun, and I’ve decided to improve the next. I took inspiration from what I’ve learned in the book The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter, Updated and Expanded [Michael D. Watkins] and applied all of this knowledge to the journey of my Talkdesk onboarding.

Your first day starts at the moment that you decide to accept an offer.

When I accepted the offer from Talkdesk, by Portuguese law, I had to give my previous company a two-month notice, which is a lot of time. So I’ve taken advantage of that time to prepare myself for a smooth entry into the team and the cluster, especially because this was my first time boarding a new company in a manager role.

During the interview process, the hiring manager was transparent about the cluster and the company, allowing me to preview my future by presenting his group’s current and future org chart.
A couple of weeks later, I got a call from HR, and they were scheduling an offer meeting. During that meeting, my manager was open to answering any more doubts I could have before my starting date. That was the hint I used to ask if we could hold pre-onboarding one-on-ones, which was uncommon. There was some resistance initially, but my hiring manager eventually agreed to have those meetings.

In retrospect, my manager agreed that was an excellent decision since I could gather more context on each meeting we held. He also pointed me to any public information about the company that I could learn. For example, I could take the Talkdesk Academy courses even before I got to the company, which allowed me to become more familiar with the product. These meetings were constructive because I was already aware of cluster challenges and what goals my future team would have. For instance, we faced issues with a provider, so our goal was to create a layer that could abstract our product from a given provider. On the other hand, there were also discussions about creating our own provider.
As a bonus, I even had some insights about the people I would manage, which allowed me to be very prepared before I arrived at the company.

You can also have these meetings with your peers. If you are a manager, I also recommend (if you can) meeting people you will lead. In my case, I got in touch with two peers that interviewed me during my hiring process. I opted for quick individual interviews with them. I had a lot of questions and information requests:

  • How do the teams work?
  • Information about my peers that I couldn’t get hold of.
  • Which teams/clusters we would be working closely with.
  • The company culture.
  • Some tricks & tips peers could give me.

With a couple of calls during those two months, I got a good head start before I stepped inside Talkdesk. If you are about to accept an offer or are in the process of joining a new challenge, try to see if there’s any availability to talk with your future manager or peers. This way, you already have a head start when you reach day one, and you will have less friction trying to ramp up.

The First Week and Month

I remember, in my youth, going to a swimming pool near the camping park where my family spent many of our summer holidays. That swimming pool had a diving platform. I can’t forget the feeling of climbing to the top platform and looking down. From that point of view, the water looked darker, which gives you the impression that you will have a considerable fall from there because it seems so much darker than it looked when you were on the ground. That view was so imposing that I had butterflies in my stomach, but I took a deep breath and dived. While you are falling and after making a splash in the water, those butterflies are gone, and you have the rush from having made it, and you feel happy and excited from doing it. That’s how I describe how I feel each time I’m on the onboarding day.

The first weeks aren’t the time to make a splash. Instead, they are an excellent time to continue your research. If you did your pre-onboarding work, they are a perfect moment to validate all the facts and theories you already have about the topic. Otherwise, it’s time to jump into the pool of knowledge by using the strategies I’ve previously mentioned: hold interviews with everyone you meet and try to gather all the information you can.

Even if you aren’t a manager, it’s an exceptional time to get to know everyone.
In my case, I joined the company near Christmas time, which was a slow time in the company as people use this time to take their vacations. Therefore, the regular onboarding inductions during my first week were pushed forward, and I used that free time to get to know the rest of my peers and my team. After a general presentation to the group, I held one-on-one meetings for each of them. I’ve held meetings with all my peers and my manager counterparts in Product areas, and I even had a couple of skip-level one-on-ones.

On these one-on-ones, you should have some script that should cover the following topics:

  • Company culture: the way of work, any unwritten rules, and best communications methods in the company.
  • What are the current challenges in the team/cluster? This is a good one to confirm or find more information that can make you more confident that you made a precise diagnostic about the new world you just joined.
  • If you were in my position, what would you do? It’s a fascinating question that can sometimes open some doors you might not be aware of.
  • About the person: pretty standard questions background of their tenure in the company. This is a good one to understand who are the people that you are going to work with, any common grounds, and even some details about their tenure with the company. Sometimes these meetings will help identify who the leaders are off the record, and even figure out who’s the company or team historian or encyclopedia that can tell you the company goes to the place it got.

I think covering these topics will gather and crosscheck all the information because that information will help you learn how to navigate the company in the following months. If you need to take notes, they will help build your mind map about the company and your department.

The First Achievement

With all this research, you should already be in your second month. You should already have a thesis about your company by this time, especially in your specific context.

You know that a good thesis will need proper validation! It’s time to put them to the test! You should present your thesis to your manager, a peer, or any people you see fit to give you good feedback. By doing these exercises, you will have a picture that matches the current reality of the place you joined. The more refined facts you have, the better your decision-making will be, which allows you to define the best first endeavor you should take.

You probably found things that could change or improve, and maybe figured out what challenges should be tackled in the future. Already have a list? Excellent!

It’s time to decide which topic to tackle first, but consider one thing: this first decision should be of adequate size. Going with the low-hanging fruit will not create enough momentum for you, while choosing a Herculean can be a recipe for failure and a tarnished image of yourself. Therefore, you should select a task that isn’t genuinely mundane but isn’t also super complex as your first achievement.

In my case, I can’t genuinely pinpoint the first achievement.
I was hired with a specific goal in mind, so I didn’t have a lot of room to pick my first achievement, and I had a chance to achieve it since that made this project scrapped. Although my purpose has changed, I believe that I was able to create some changes within the cluster, which allowed things to get moving.

I was able to share a lot of my knowledge about hyper-productive patterns with all the teams in the cluster. This reflects how I was able to spin off a team from an existing one, while maintaining an open door to cooperation and collaboration. Both teams now look like one team virtually, which is a bit inspired by the LeSS framework. This was possible because I had an amazing peer who became a good ally with these changes.

The 90-day Mark

You just made it to the 90-day mark by this time. We don’t expect to be utterly savvy with the company details. This is an unreasonable expectation.

Around this mark, you should have a pretty good map to navigate the company, understanding who is the point of contact, the “shot-callers,” and the influencers. You will have a good picture of the company status (especially in your specific context), secure your first achievement, or be almost there.

If you complete everything, you will have the tools and the momentum to make an impact and enjoy the benefit of setting yourself up for success.

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Techie by default but on the side used to play on the Portuguese league gridirons (and got awards from it), but I've traded my pads and helmet for a bicycle.