User-centered digital transformation

1. Assemble the Team

The size of the team really depends on how big the company / division is. At the minimum, you should have an individual from each of these core areas (keeping in mind that sometimes a single person can fall into multiple areas): an owner, driver, stakeholder, and super user:

Owner — In a small business, the owner is the usually the literal owner of the company, but in larger businesses, this is the owner of solution. If it’s a complete business process software, it should be the CEO. If it’s just project delivery, then it’s the head of projects. This person will guide the development of current workflow, identify problems of today, find the solution criteria, aid in the roll-out, and communicate the change to the team.
Driver — The person who is most deeply involved in the organizational process such as the VP of Operations, Professional Services, Chief Technology Officer, or sometimes the Project Manager. They will be the one who requests the software trial, be the main point of contact for questions, and lead the workflow and requirements design. Often, the owner wants to also be the driver. Try to separate these two roles out so that one person can focus on the project management of finding and implementing a new software and the other can focus on the vision and feel of the new solution (the owner).
Stakeholders — Those whose work life will be significantly impacted from the change and who you need official sign off from. Typically consists of Finance (admin / CFO), Sales (head of sales, Accounts team representative), and Support Manager.
Super user — Those who are optimistic about change and quick to adopt new software. We will want end users such as a Designer, Consultant, Developer, or Analyst. They will be very important in Week 5 & 6 when we establish the core user stories and search for red flags within the solutions.

2. Map out Today and design the Future

In this phase, you’ll determine the tools & business flows of today and what you’d like them to look like in a new solution. Then, you’ll find out what your team members are doing today and what their ideal work day / week / year would look like in a new system.

Tools & business flows

Time & Expense billing for a Business Consulting Firm (Visio)

Today: Take an inventory of the tools and processes your team is currently using to do work . These tools normally fall into three buckets: 1) Business tools such as Asana, Harvest, Google Apps 2) Craft tools such as Sketch, InVision, Photoshop, Sharpie 3) Personal / periphery tools such as Moleskin to-dos, Workflowy, calendar app.

Now look at the Pros and Cons of each. Let’s take a look at Asana

Pros: Super fast and easy to collaborate
Cons: Doesn’t link to Gmail conversations with clients.

Future: Now, it’s time to design the ideal workflow of how the internal team will operate and how you’d like to service your clients. Some common tools to use are Mural, Lucidchart, Keynote, Visio, and Sketch.

Web Development Studio’s Services & Operations Workflow (Lucidchart)

IT Consulting Project Reporting Process (Sketch)

Bookkeeping and CPA Firm (Draw.io)

User-based workflowsYour goal is to determine the daily life of a team member and what they need to do in order to be successful. You can think of each team member (user of the system) like a part of the company’s body — the heart, the lungs, the veins. Like a vital organ, each person in a company has their own needs to produce the desired output to help the entire body function.

You can phrase these user needs using the following sentence formula:

As a [person], I [need], so that [personal / company success metric].

Today — the current user story. As an owner, I have no visibility into how busy my team is, where I should bring in new business, and where we need to hire new employees. This is helpful for identifying places of improvement.
Tomorrow — what the user story needs to be for personal / organizational success. As an owner, I need visibility into how busy the company is so that I know where to sell more services (to make more money) or hire (so that we can continue growing in popular requested areas). This is helpful for visualizing the ideal solution or platform.

3. Search for the solutions out there

Now that we’ve determined our basic structure and user needs of today and what we’d like them to be, it’s now time to start the search.

Put together a Software Search Google Sheet on Monday to start collecting information on reviews, features, and company stories. You will use this to refine your research from about 20 vendors to hopefully around 6 this week.

Reviews

Review sites are for collecting a large list of similar software names in a list. And that’s where reviews site’s usefulness tends to end. Often, they are put together by people not experienced in the industry or reviews are paid for and are skewed towards 5 stars.

Though, review sites are good for red flag comments — ones that warn a certain user type, a poor experience, functionality that was promised on the website but didn’t perform in the application.

The most honest reviews sites aren’t actually review sites; they are:

Blog posts by professionals in the industry such as Teamwork PM by Netwise and Slack vs. Hipchat by Crew
Forums such as SEO/PPC Project Management on Reddit or Resource Planning on Quora
YouTube search “Review” “Demo” or “Tutorial” such as Asana vs. Podio by an SEO agency, Harvest Getting Started by Brian Bruce, Mavenlink Tutorial by Michelle.
Wikipedia: Comparison of PSAs and then specific company articles such as 10,000 ft
Slack groups such as the Bureau of Digital’s #dpmtools channel.

Feature Categories

Stat compiling a list of feature categories that you’ll need such a project management, time tracking, and utilization. We are just looking if the software has it or not. Best found under “features” on the customer’s website. YouTube is another good resource for skimming through features. The 30-minute overview demos tend to be a good resource because they are showing screenshots and workflows. (watch double speed or click in 1-minute increments). Lastly, New features can usually be found on the blog or on their support site.

Company Story

Beyond the software, it’s important to know about the founding of the company and where it is heading. While it might be the best option today, it may be trying to move into a new category away from your core business, or it just got purchased by a private equity firm and no new development is happening. LinkedIn and Wikipedia are good places to start if their About Us page is too general.

Friday Meeting

Have an internal meeting Friday afternoon. Take the 20 or so solutions that you found and narrow down to 6. Don’t forget to put your Status Quo in your comparison — it’s always a viable option, especially if you can upgrade / augment with add-ons, API, and/or new processes.

4. Discovering business fit with quick trials

Moving into week 4, we are not quickly testing the solutions. The goal here is to test for basic match of your process and user needs while getting a feel for the UX.

The Driver will sign up for a trial. If the software doesn’t offer a free trial, they will usually have a request demo or request a trial. In that case, fill out the form: they are trying to screen you (have a quick call) to make sure you’re a good fit for the product. Once a sales rep reaches out to you, ask for a trial so that you “can come to that initial call knowing more about the product.”

If they don’t let you into a trial, this is a red flag. All leading SaaS solutions offer a trial because they want their customers to be best equipped to make the right decision… and choose to stay with them for every month thereafter.

Quick testing

The Driver should block off an hour for each software. Don’t worry if you don’t finish certain things like setting up a project or invoicing the customer — this is a blitzkrieg on the software. There’s no expectations for how far you get. And remember, not all software can do everything, so it may not be you.

This is what you’re trying to do:

Feel how the layout of the software ties into the solution’s philosophy for how you should work. They will probably have example data in the system, so just click through and see what’s in there. If there’s a tutorial walkthrough, go through it. Even if it seems slow, you’re probably saving time in the long run and you’ll get to see what they think is unique compared to competitors (6 mins).
Setup stories (likely admin / manager roles) such as billable and cost rates, work weeks, skills, project templates, and permissions (6 mins).
Get things live. If it’s just a project management tool, get at least two very different projects live such as Website Development and Monthly Social Media Campaigns. If it’s business process platform, get a live client running with contacts, sale, quote, project, ticket, and contract / retainer (10 mins).
User stories + process. Now that you have everything (or at least as much as you could) in place, it’s time to run through a day-in-the-life along the process. User story examples include: As an Account Manager, I need to enter in a new sales opportunity and follow-up after meeting a potential client at a conference so that I can close more next quarter. As a Project Director, I need to convert proposals to project plans so that we can execute on what we promise (10 mins).
Notes and thoughts. In the Software Search Google Sheet outlined above, write out what user stories worked and what didn’t. It’s very helpful to have screenshots for when you come back to this because all of the tools start blending together. Start your list of concerns/ questions at the bottom. This will be your team’s running notes that you can share with the software vendors.

Beyond a trial, it’s good to get your hands on a demo site so that you can run higher-level user stories faster such as project status updates, utilization, financial forecasting, etc.

5. Validating core user stories — Will it work for us?

In week 5, we’ve tested the software for a week and will hop onto a screen share with a small number of software vendors that have past the tests of week 4.

Create a software evaluation document at the beginning of the week which includes everything we’ve found so far: current process and tools, current and future ideal user stories, and our notes of on this software.

Share your the internal team (we have the owner, the driver, and a stakeholder in the process by now) as well as your potential vendor’s sales rep.

Send this document to everyone before the call so that they come prepare and so the vendor’s rep can answer any questions or address concerns before the call.

Software Evaluation Google Doc

Discovery Demo Q&A

Screenshare through Zoom.us (my favorite), Uber Conference, Join.me, or GoToMeeting. You’ll have two tabs open, your Software Evaluation Document and the application you’re trialing. Share your screen so that you can have control of the conversation.

Review your high-level company info such as company background, who’s on the evaluation team, what the timeline looks like.
Current tools: pros / cons. Any questions?
User stories: review common workflows. Any questions?
The demo will go through the company workflows. And where, within the user stories, your team was getting held up (Questions — User stories we couldn’t figure out)

Debrief

Does it have the basic features? Review requirements doc — especially the really important things that have 0s.
Does it work like I work? Review your workflow diagram — ask what they can do, and what they do better than their competitors.
They should have pricing and onboarding programs on their website, but if they don’t, ask for an estimate.

Friday Meeting

The owner, driver, and stakeholders will have sat through 4 of these Q&As, hopefully all in the same week. It’s time to bring the options down to two (plus status quo).
For the next hour, review how the software meets the workflow, user stories, and requirements needs.
Take a break. Rank them from 1 to 4.
For the following session, you will invite your core super user team to the conference room. Present your top 2 options.
Quickly show the documents that you’ve put together, the methodology, and where we are going with it. (10 mins)
Demo of Option 1 overall workflow (10 mins). Highlighting the organizational value of the software. Then show what we are asking from you to do for the next week (10 mins): Track tasks, Email, Log time.
Questions (10 mins)

Repeat for Option 2 (30 mins)

https://asana.com/guide/help/organizations/members

6. Using it for real and looking for Red flags

The Evaluation Document has now gotten bigger.

After the first day of evaluation, send a survey to your team, similar to this one. Or, you can just share them on the running document (but it’s getting big, so it might be confusing).

Team member’s name: Rakhee, QA / Developer
User story: As a developer, I need to easily log time on Friday for the clients that I’ve done work for so that I am communicating the value that I’ve created this week.
Like: That tasks I’m scheduled on automatically show up — that saves me a lot of time filling out the timesheet.
Dislike: How cluttered the screen was — and can’t see which client I did work for very easily.
Outstanding questions / confusion: Why is it showing as billable time on a non-billable task? How do I move time to another project if I accidentally log that time somewhere else? ‘

If you can answer the questions, then great, answer them, or go over to their desk to help them out. If it’s too complicated, share the vendor’s sales rep on the Google Doc for them to answer inline. If it’s too complicated for that, table the questions for the group Q&A later this week.

While your team has started using it for real, it’s still just a trial. We’ll also want to talk to another company who is actually using it for real. The best place to find this company is through the software company’s case studies page. Look for companies that are most like you — provide the same service, were relatively the same size when starting, talk in the same way, moved from the same tools, were trying to fix the same things.

When you’ve found that fit (let’s say that Big Blue Digital is that match), ask your sales rep to speak to the main person in the case study (Brendon, the CEO). They will do an introduction and you can spend a few minutes talking to that person. You’re looking for red flags here — so ask them about the red flags that you’ve found in your own evaluation: a user story that’s not fitting, a piece of your process that doesn’t fit in the software.

Final document for debate:

Feature Requirements: Since, by know, you know what features are needed to support the workflows and user stories, you can put together a detailed requirements document with % fulfilled.
User Story Fit: Here, you’ll take all of the user stories that you’ve discovered in the process and put the two solutions against each other for fit with your user’s needs.
Business Case: You can take a higher-level approach and write out a quick summary of the value of the new solution and if it’s worth making the change.

Make the decision using the final document as the backbone of the conversation. We are trying to take emotions and knee-jerk reactions out of the last few days.

7. Planing the digital transformation

The last step in week 7 is to sit down with your internal team and the software company that you choose to review the goals for the new system, the timeline, the people involved, and any data migrations needs you have.

Congrats, you’ve made it to the start line of creating a modern digital service business!