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Convincing a higher-up to buy into new software is rarely an easy task, but it can have a major payoff if done right. At AvePoint, I was lucky enough to have a hand in developing the template to get our Microsoft Teams environment off the ground for the entire North American Sales team. The process is different for everyone, but there are several common threads throughout all Microsoft Teams adoption cycles. Here are a few handy steps I’ve learned to help get your boss on board.

Phase One: 

Accept the Role of Champion

If you want to convince your boss that Microsoft Teams will help your team communicate better, you must prepare to step into the role of a champion.

Not only are you going to be advocating for Microsoft Teams adoption from your boss, but you’ll also be appealing to your team. To do this effectively, you’ll need to assume a number of other roles including:

  • Architect: You’re going to be the one coming up with how the channel should be structured and how the tabs should be.
  • Migration engineer: You’re going to be the person to coordinate content getting into the Teams environment.
  • Ongoing trainer: You’re going to learn about new features, promote them internally, and train team members equally so everyone understands the new technology.

Assess Your Current Collaboration Process

How effectively is your organization collaborating right now? What types of systems are you using and how are they working out for everyone? Whether you’re primarily using email, Slack, or Yammer, try to any pain points that need to be addressed.

To get your boss onboard with Microsoft Teams, you’ll need to understand how your business operates and figure out where the chinks in your communication chain are. Consider the major projects you’re working on where everyone needs effective communication tools. What do those daily workflows look like? What are those every-single-day discussions and reviews your users have to deal with in specific documents that are getting passed back and forth via email?

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Create “The Ideal Prototype”

Next, you’ll want to create what I call the “ideal prototype” based on your unique work environment. The goal here is to design a prototype specifically tailored to your business needs. Here’s some general advice to keep in mind during the design prototyping process.

Think long-term when naming Teams. Names for business units, major conferences, and regional offices are all great options for Team names. The key is to represent what the Team is actually going to be about instead of a momentary hot topic project. We discuss this more in detail in our previous post.

Create channels based on static interest levels. Similarly to Team naming conventions, ensure that every channel in a given Team is created around a topic that’s going to have a static interest level.

For instance, instead of building a channel for each weekly update of a major project (leaving dozens of channels deserted as time goes on), consider making a channel dedicated to that project with the weekly updates as threads inside. Topics like updates will garner plenty of buzz at first, but that level of excitement will constantly change; the project itself will have a much more consistent level of interest overall.

Surface important data in tabs. Whether it’s key documentation, user guides, or project schedules, you want to ensure that regularly viewed info isn’t buried inside the Files tab. Surfacing applications and documents as their own tabs will be much more efficient for anyone planning to immerse themselves in a Team. Including this in the prototype will show your boss how much time he/she will be able to save at a glance. No more digging through emails or sifting through Slack channels to find the relevant information; it’s all right there at their fingertips.

Consider feedback from your team. Lastly, it’s always helpful to workshop your prototype with your team members first. Iron out issues, try to brainstorm additional ideas you might’ve overlooked on your own, and try to find other potential champions who are just as enthusiastic about bringing Microsoft Teams to your organization as you are. The worst thing you can do is operate in a bubble.

microsoft teams

Plan an “I’ve got an Idea” Meeting

Once you feel like you’ve gotten a good understanding of your organization’s needs and how you want to handle your rollout, it’s time to schedule what I call the “I’ve got an idea” meeting (a.k.a. the pitch meeting with your boss). Since you’re going to pitch an idea that will essentially change the entire workflow of your business unit, you’ll need to come prepared. Make sure you bring:

  1. Your ideal prototype
  2. The list of people you talked to and workshopped the prototype with
  3. Any feedback that arose during the workshopping process
  4. A thorough outline of how your business communicates today
  5. A detailed explanation of how this new prototype is going to smooth out some of those issues.

Follow Up After the Meeting

Ultimately, the reaction to the pitch will go one of three ways. If your boss turns down the idea due to it “not being a good time right now,” don’t take that as a clear-cut “no.” Figure out if it truly is a timing issue (is your organization is in the middle of a major project, for instance?), and if so, simply try again later. Be sure to actually follow up if the problem is time-related.

If the reaction is more based on uncertainty around how your organization could safely make the leap to Microsoft Teams, it’s time to hit the web and do some research. Common concerns regarding governance and content management can be handily addressed by third-party solutions.

If the best-case scenario plays out and you get the green light, it’s time to move forward to the next phase of the rollout.

Phase Two: Refine, Implement, & Train

Now’s the time to do a bit more fine-tooth combing. Phase two is all about making the switch as smooth as possible, working with members of IT to see what their takes on Microsoft Teams are and how best to cater to them, and working with individuals who are struggling with the new technology.

Schedule the Switch

After any additional planning and workshopping needed, the next step is to work with your boss and IT to schedule the switch. As champion, you’ll need to volunteer as the one who’ll work with IT to figure out the best way to transition from your current processes.

Using a certain email distribution model? Maybe a channel can be used for that now. Leveraging file share repositories? Perhaps IT can migrate that content into the backend SharePoint site repository for a channel. Have certain permissions on key documents? Work with IT to ensure those stay persistent when you migrate that content over into Microsoft Teams. The goal is to minimize workflow interruption as much as possible.

Promote the Switch

Next, the challenge will be getting the rest of your organization on board. To do that, you ideally want to get your boss to propose it to the rest of the company. Though you did the legwork, it’s important for your boss to feel ownership of the idea and for him/her to present it as if it were their own. The more authority behind the decision the better, and the farther reach it’ll have throughout the organization.

Train Your Users

Whether it’s before, during, or after adopting Microsoft Teams, everyone in your organization will need to be trained. As champion, you’ll be in charge of coordinating this. I suggest:

  • Distributing general information about what Microsoft Teams is
  • Referring users to blog posts, webinars, and eBooks from trusted sources
  • Put on demonstrations in demo environments showing how to handle threads, tabs, Team management, and so on
  • Seeking out those who seem to be struggling the most and schedule some one-on-one time to work through their challenges and/or apprehensions

Remember, you have the boss on board at this point. Leverage that authority to enforce that this software adoption is an organization-wide move towards better collaboration.

microsoft teams

Long-Term Training & Support

Once everyone is on board, the switch has happened, and employees are in the process of being trained, all that’s left to do is facilitate ongoing user training and support. Though we just went over training above, support is just as important. People are going to mess up, and how you respond to that can be the difference between a confident user and a begrudging one.

Publicly encouraging good usage is essential. Even if someone simply makes or replies to a thread correctly, give them a shout-out. There are even apps that allow you to give kudos to users in Teams based on their actions.

Conversely, if you see someone doing something you wouldn’t consider correct, try not to shame them in front of everyone. Instead, reach out to them in the individual chat and, using the copy link feature, share a link to the message they may have posted incorrectly and show them where they made an error.

You’ll need to maintain this string of coaching and supporting users for anywhere from 6-12 months as your organization gets used to the new technology. Even then, however, Microsoft Teams is always growing and adopting new features. If you want to keep up with all the latest changes, I highly suggest following Microsoft Teams experts and official accounts on LinkedIn and Twitter. Tools like Microsoft Stream can even help you distribute user guides and announce updates to the entire company!


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