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Future of Work

Find the right strategy to upgrade your workplace, digitally

You could start your office evolution tomorrow. Find the right digital transformation strategy today.

Workplace digital transformation isn’t just the latest long-winded buzzword. It’s a commitment to a better work environment with digital tools that make the workday easier. It’s a movement many companies have already begun. And it’s a trend that isn’t slowing down anytime soon.

“The pace of change just in the last few years is comparable to the prior fifty.”

Mary Beth Westmoreland, CTO at Blackbaud

A lot of companies understand they need to start moving their workplace towards a digital transformation. But many are left scratching their heads as to what transformation strategy to go with. Of all the digital tools out there, what are worthwhile investments? What takes priority? How do you come up with a strategy for all of it?

Here are six questions to ask your company and your team of stakeholders to find the right path.

1. What are the digital technologies employees crave?

Go straight to the source. Digital transformation in the workplace will significantly affect every employee, so make sure they’re involved in the research and decision-making processes. Here’s how:

a. Survey

Send out a company survey. Keep it short but make sure you cover enough ground to get a full picture. Use multiple choice so employees can simply choose pre-selected answers, with an optional “other” or “notes” section to fill in additional info.

Employee survey questions could include:

  • What daily processes take up an unnecessary amount of time? (signing documents, entering POs, submitting PTO, etc.)
  • What are the most frustrating aspects of the office? (meeting rooms, printers, IT tickets, etc.)
  • What are your favorite tools? (Slack, calendars, project management software, etc.)
  • What are your least favorite tools? (digital asset management, email, ERP, etc.)
  • What are tools that you used in a past job that you loved? (Slack, Trello, 1Password, Spoke, etc.)

b. Advocacy group

advocacy group for workplace digital transformation strategy
via Pexels

In addition to the survey, you can also form an employee advocacy group or committee. Ask managers for a few colleagues that might have extra time and give ample feedback whenever new ideas are introduced.

Make sure the advocacy group has a solid mix of departments, job levels, genders, ages, and general backgrounds. Put together a calendar of meetings and set an expectation for their commitment up front. Plan on meeting once a month with easy-to-answer emails sent out in between if fast feedback is needed.

Once the company survey is completed, share the results with the advocacy group and draw additional feedback from them on areas of the office that were called out. Avoid a tool-bashing session by asking, “What would the ideal process look like?”

Later on, when you decide on the digital tools you’re going to invest in, check in with the group on major updates and gather as much feedback as possible using them as user testers.

c. Shadow colleagues

Lastly, if you have enough time, shadow a few different employees observing the office frictions in real time. Some of them may be encountering roadblocks to productivity without even noticing, so observations with live convos can be helpful to identify the biggest issues.

Dedicating a day to spend a few hours with a couple of different employees can go a long way to finding the right kind of digital transformation strategy for your workplace.

2. What are all the current tools and common processes your company uses?

Working with the dedicated project crew or group of stakeholders, list out all of the tools your company currently uses (+ budget, contract expiration date, etc.). Add to the list any additional processes that don’t have a specific tool yet but are integral to the business.

For tools you already have implemented, rank their effectiveness based on the employee survey and the group’s assessment. For processes that don’t have tools, rank their priority. Perhaps signing documents isn’t a high enough priority to get an e-signature tool, but maintaining order when colleagues are hot-desking is enough to get a desk scheduling tool.

Once you have identified ineffective tools and processes that are a big priority, start to do some industry research on the best replacement options. Sites like IT Kit can be helpful to jog ideas.

3. What are the major pain points?

Add a column to your list of tools and processes to bullet out the major pain points of each, based on surveys and internal group knowledge. Pain points could include:

  • Complicated setup
  • Difficult to use
  • Slow to use, too many steps
  • Inaccurate
  • Not intelligent
  • Wasteful

Maybe your digital asset management system is wonky and hard to search because downloading images takes too many steps or clicks.

Oftentimes meeting rooms are impossible to find without a tool to manage them because people steal rooms and don’t show up to others.

Knowing what makes something difficult to do will help you when picking out a new tool to alleviate the issues.

4. What will have the biggest impact?

Gartner CEO Top Business Priorities Digital Transformation
Corporate structural development and IT-related top the list: aka digital transformation. via Gartner

Rank each opportunity using the ICE score system (impact, confidence, and ease), but focus predominantly on impact. The most impactful upgrades should be your top priority, regardless of how confident you are in carrying it out or how difficult it may be.

Then focus on the easy wins, like a new password manager or visitor system.

Combined, these will have a big positive effect. Separately, the easy wins early on will help get buy-in for the larger initiatives down the line.

Blackbaud’s CTO Mary Beth Westmoreland asks herself this question when prioritizing tools:  

Mary Beth Westmore Digital Transformation Quote
via Samsung

5. What are your company values?

Robin Core Values Workplace Digital Transformation Strategy
A few of Robin’s core values. See the rest

If you preach transparency but don’t use an open file storage system, change that.

What are your core company and brand values that you publish internally and externally? Make sure your workplace’s digital transformation aims to match those.

If you’re all about “innovation” in your brand and product messaging, but don’t have meeting rooms equipped for video conferencing, what does that say to your employees, visitors, and partners?

Identify the tool and process opportunities that match your values and make those a priority as well.

6. What kind of budget and timeline can you commit to?

Dilbert Technology Budget Workplace Digital Transformation
via Dilbert

This question is the big one, that often sidelines projects temporarily, if not permanently. If that becomes an issue, figure out longterm if it would cost more to carry out the same initiative down the line. Oftentimes the answer is “yes” so you can show off the cost-saving benefit of rolling something new out now vs later.

As tech companies, we need to be thinking in the longer term, not just the shorter term. We might look at a technology and think, ‘Wow is that really going to help me today?’ Well, If we all live in the today we’re never going to get to the tomorrow. Right?

CTO Mary Beth Westmoreland of Blackbaud

Plan on also having a more flexible approach to budgeting, based on the ROI of the digital tool(s). If you’re planning on investing $10k in a new SaaS tool but the best option is $20k, maybe it’s worth it in the long run.

We’ve all been there before when a company buys a cheaper version of a tool and the stress and time wasted on the lesser version far outweighs the slight difference in cost. Don’t be that company.

The timeline part is really just to keep you and your team honest. But be realistic. Oftentimes projects can take up to 4x longer than anticipated. If you’re publishing go-live dates, you might want to pad that in case things go awry in the process. Otherwise, the project may become the butt of jokes if the date continually changes.

Now what?

Workplace digital transformation, commence. Depending on the budget and priorities, you should have a nice collection of tech tools that you need to go and source vendors for. Ideally, your list has a mix of easier wins and more complex projects.

For the easy wins, check out sites like IT Kit and Capterra to determine what you want to go with.

For the more complex projects, you might want to do an RFP to ask vendors more specific questions associated with your business. (If you’re doing a meeting room display RFP, we can help with that.)

And when you’re done with implementing that first set of tools, you can get started on the next batch, assuming they’re impactful enough to invest in.

A few pieces of advice:

  • Know when you need an off the shelf solution vs a custom one
  • Watch out for consultancies. If using one, go by word of mouth and get trusted advice and referrals from companies that have done the process well

workplace digital transformation strategy

Sources: Vecteezy, Samsung Business, Pexels, Gartner, Dilbert