Cactus Bright

How to pick the right tools for your team

Finding the right tools for your team isn’t easy. You need to have a mix of strategy, rational decision making, good judgement and some intuition.

In this guide, you’ll learn how to pick the right tools for multiple teams and get buy-in. We’ll walk through how to:

  1. Identify the problem.
  2. Measure the problem.
  3. Convince leadership.
  4. Get a team of workflow experts together from each team.
  5. Research and test tools.
  6. Present the tools.
  7. Pick the tool.

Resources:

What this guide doesn’t include:

This guide will work best for:

When I was a data analyst in working in professional services, we had to jump between five tools just for the project intake. Some of the tools were glitchy or we didn’t have the right permissions. This is a pain point for many teams leading to frustration, bitterness, delays and mistakes.

If you don’t have a good tool stack, it’ll cause inefficient processes and scattered tools. The operational debt builds up and affects everything that’s built on top of it. Having a good tool stack gives you a solid foundation to build processes on.

Now that I’m in a position to make tooling decisions, I make it a priority to pick the best tool (within circumstances) for the teams I’m supporting. Here’s how.

1. Identify the problem

Imagine you’re an implementation manager and you’re looped into a potential project.

You go through this for every project and it’s extremely frustrating. This is how you identify problems. Frustration is a tool if you learn to use it rather then descending into anger and hopelessness.

〜 To identify problems as an individual contributor:

  1. Notice how you’re feeling as you’re going through certain processes.
  2. Name the feeling — is it frustration? Anger? Hopelessness? Stress?
  3. Focus on the problem that’s causing the feeling. What exactly is causing the feeling? What would make things feel better?

〜 To identify problems as a manager:

  1. What are people complaining about?
  2. What are people frustrated about?
  3. Are there consistently mistakes?
  4. Are deadlines consistently being missed?
  5. Are teams blaming other teams?
  6. Has people who usually give you feedback gone quiet? If outspoken people have gone quiet, this could mean that they’re losing hope and feeling powerless.

2. Measure the problem

When I was a solutions engineer, we didn’t have a process or the right tools for project intake, quality control, and deliverables. One project took 51 emails, 46 hours, and 4 teams to confirm the specs. Projects were consistently delayed, we made a lot of mistakes due to incomplete specifications, and had to re-do projects multiple times.

We feel these pains first-hand as the person doing the actual work, but how do we get the attention of management? This is where measuring the problem will help. Your manager will have to explain why this matters to their manager, and data can help when first-hand experience is missing. Measuring things will show managers the numbers, time to value, and the impact of the problem.

〜 Your measurements will vary depending on the context, but here are some things you can track:

3. Convince leadership

You can either do this before or after you research tools. The scenario I’m showing here is to get buy-in before deeply researching tools. When multiple teams are involved, you’ll need to get buy-in from multiple leaders. If you can’t get buy-in, then you may be wasting your time researching tools.

〜 Depending on your team structure and dynamics, you’re going to have to convince leadership that:

  1. The best solution to the problem is tooling and you have proof that you’ve tried other things to back this up. The tool should reduce work, not add more work.
  2. This is a problem worth fixing. That it’s worth spending money and resources on.
  3. Stakeholders are on board.
  4. You have a plan and can take this on.
  5. There’s a potential return on investment.
  6. The need for a tool aligns with the company’s goals and priorities.

〜 There are a lot of ways you can get buy-in from leadership, and what has worked for me is presenting this information (in no particular order):

  1. Scope of the problem including the measurements
  2. Risks if we don’t do this
  3. Before and after
  4. Options, including any preliminary tooling research
  5. Limitations of our current solution and the affected teams
  6. Next steps
  7. *Extra: Potential high-level cost estimates

This is an example of a flowchart I made to show leadership our future if we stayed on the current path. I wanted to show them how unmanageable the problem will get. Flowchart Example

This is an example of how I presented the limitations of our current process. I highlighted the biggest problems in red and only talked about those. The other limitations are included so leadership can have a visual of how large the problem is. LimitationsExample

4. Gather workflow experts from each team who will be involved in choosing a tool

Once you get buy-in, it’s important to include stakeholders early on in the decision making process. This gives them more skin in the game, helps them understand decisions that they can communicate back to their team, and will help later with procurement and adoption.

Remember that people have other jobs, so it’s your responsibility to make sure they know their role in this and to make it as easy as possible for them to participate.

〜 Who you should include:

〜 Their responsibilities:

〜 Your responsibility to the workflow experts:

5. Research and test the tools

Now here’s the fun part. Make sure you trial tools and don’t depend on only marketing content or sales people.

〜 Do your research:

  1. Sign up for trials whenever possible. For some enterprise software, you may have to reach out for them to set you up with a trial.
    • This will help you test the user experience.
  2. Use a weighted system so you have a non-biased way to assess tooling. Here’s a template of the system that I use.
    • How do you decide what features you need?
      • Start with a tool’s feature list. Every software has a pricing page with a list of features.
      • Customize the list based on what you know each team needs.
      • Ask the workflow experts to review the list and add / remove things.
      • Update the weights based on importance for each team.
  3. If your company has strict security protocols, eliminate tools that don’t meet the protocols.
  4. Does the tool work well with existing tools?
  5. Does the tool integrate with what you need it to?

〜 Once you’ve narrowed down the options to the top 3:

〜 Some things to watch out for with sales people:
Sometimes they will straight up lie to you. For example, if you’re looking for specific integrations, make sure they actually have an integration and it’s not just on a roadmap or via a middleware that you have to pay extra for.

6. Present the tools

Once you have the top 3 tools, it’s time to present them and have a discussion.

〜 Here’s what you can include in your presentation:

  1. Recap of why you’re going through all this.
  2. How you picked.
  3. Summary of the research.
  4. Specifications of the top 3 tools:
    • Number of features
    • Number of workarounds
    • Number of features missing
    • The weighted score percentage for each team
  5. A table of ‘flaws, but not dealbreakers’ for each tool.
  6. A breakdown of each tool.
    • Why the tool?
    • Known compromises for each tool
    • Known limitations and workarounds
    • Known extra costs. For example:
      • API access and middleware
      • Implementation
      • Sandbox
      • etc
  7. Pricing (if you’re at this stage already)
    • If you still want to narrow down to the Top 2 tools before getting pricing, then follow the same categories above and just add in pricing at the end.
  8. Q&A
  9. Next steps

Here’s a basic slideshow template that you can build off of for your presentation.

7. Collect feedback

After each demo and presentation, make sure you give the team opportunities to give feedback via a live discussion and asynchronously. Async communication is there for people who are not comfortable expressing their opinions in front of a lot of people.

Give people the option to send you feedback via Slack and email as well. The goal is to make it as easy as possible for people to give feedback. Gather everyone’s feedback into a centralized document where you can handle conflicting feedback and prioritize suggestions.

8. Pick the tool

If everyone feels comfortable with the presentations and information by now, then you can hold a vote to pick a tool. The way you do this depends entirely on team dynamic. I’ve had teams where I held a formal vote, and teams where I’ve used a casual poll on Slack. It depends on who you’re working with and if there’s bureaucracy required.

How detailed you want to get is up to you. Do you need to put in place criteria for voting? What factors should the team consider when voting? For example, they could consider the cost, user experience, or integrations with existing tools, etc.

Once the vote is finished, get an official quote for the chosen tool — remember to ask for a line-item breakdown. Because of all the research you’ve done and data you’ve gathered, once you have the quote, you’ll able to fly through procurement.

Final tip

There will be compromises no matter what you choose. You can’t make everyone happy. The weighted system will help you decide which compromises has the least impact.

When you follow a strategy to pick the right tools, you’ll reduce operational debt for the company over time. Optimizing operations is an ongoing journey, and following this guide will set you on the right path. Give these methods a try and let me know how it goes!

And remember, the work doesn’t stop at tool selection. You’ll need to consider implementation and costs, change management and adoption, and continuous improvements.

How do you select tools at your company? This is a living guide that I’ll update as I learn more. I’d love to hear how others do it!

#work