About this article
Why we wrote it

After a long software search, family offices often want to move straight to implementation, and our team has seen how much smoother rollouts go when problems are anticipated first. We wrote this to set out five common technology implementation pitfalls and how to plan around each one. Before your own rollout starts, you can use it to run a short scenario-planning exercise and agree in advance who handles each risk.

How we made it

We used AI tools to help gather research and speed up the first draft. That left more of our time for checking each figure against its original report and adding what we see in client conversations. A Masttro editor reviewed every claim, and members of our team read the article before it was published.

Written by
Ricardo Wiesner
Edited by
Dan Williams
Published
May 18, 2024

Key Takeaways

After an extensive search process, your organization is about to implement a new technology. You're understandably excited, because you genuinely imagine this new software or platform as the solution to countless organizational challenges. But having helped countless clients implement such solutions—and having implemented some ourselves—we at Masttro see it as our duty to offer some sage advice:

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Do a little scenario planning.

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That is to say, before beginning any significant technological installation, it’s always worth pausing to imagine what might go wrong. No, we’re not catastrophists. We’re realists, and we know from experience that the most trouble-free installations occur when troubles are faced head on.

With that in mind, here are five most common tech-implementation pitfalls, with advice on how to minimize the likelihood they’ll occur or the consequences if they should.

  • Hidden costs quickly eat up your budget. Before you sign any contracts, ask the vendor for five examples of extra fees or upcharges. Do they charge by the hour for support? Must you pay more for certain modules? Next, create a budget that includes all potential costs, then ask the vendor to review it and provide honest feedback on what's missing based on their experience with similar size and types of organizations. Use these final numbers as your guide for the ultimate expense.
  • Your org lacks the resources to properly implement the new technology. Additions to a tech stack generally require internal resources. To ensure you’re planning properly, identify the necessary roles and responsibilities early in the process and bring the employee(s) you task to oversee the implementation into the vendor conversation. That way they can sound alarms if they don’t believe what’s coming is doable. If you lack the internal resources, ask if the vendor works with a third party consultancy that can help manage the process and make it seamless without stressing your team.
  • Your org lacks a fully formed go-to-market strategy. If you haven’t implemented such a technology it’s hard to identify the “known unknowns'' that can create issues during the rollout. The vendor, however, should be very familiar with such issues. So be sure to review your implementation plans with them, asking what elements you’re missing or underestimating. Rely on their experience to help you plan for whatever it is you don’t know you need to worry about.
  • There are unexpected technology issues. Have a separate conversation with the vendor around technology hiccups, asking for specific examples of regular issues and how they are solved: Do they have a workaround protocol or a team that handles such problems? A prior understanding of the most common issues will make it less stressful when it happens with your organization.
  • Your team hits the “implementation dip.” In his book “Leading in a Culture of Change,” educational reform expert Michael Fullan introduced the concept of an “implementation dip,” which is the inevitable “dip in performance and confidence as one encounters an innovation that requires new skills and new understandings.” Strong, positive leadership can help ameliorate and normalize difficult feelings among team members, so that everyone can remain focused on the task at hand. Also, work with the vendor to set up a series of small, easy wins for all.
Five rollout pitfalls and how to head them offHidden costs: Ask for five examples of extra fees, then have the vendor review your full budget.; Too few internal resources: Name the roles early and bring the project owner into vendor talks.; No go-to-market plan: Review the rollout plan with the vendor and ask what you are missing.; Unexpected tech issues: Ask for the common problems and how the vendor’s team solves them.; The implementation dip: Lead the team through the slump in confidence and set up small, early wins.PLANNINGFive rollout pitfalls and how to head them offCommon snags when adopting new technology01Hidden costsAsk for five examples of extra fees, then have the vendor review your full budget.02Too few internal resourcesName the roles early and bring the project owner into vendor talks.03No go-to-market planReview the rollout plan with the vendor and ask what you are missing.04Unexpected tech issuesAsk for the common problems and how the vendor’s team solves them.05The implementation dipLead the team through the slump in confidence and set up small, early wins.Source: Masttro; “implementation dip” from Michael Fullan, Leading in a Culture of Change
Five rollout pitfalls and how to head them offHidden costs: Ask for five examples of extra fees, then have the vendor review your full budget.; Too few internal resources: Name the roles early and bring the project owner into vendor talks.; No go-to-market plan: Review the rollout plan with the vendor and ask what you are missing.; Unexpected tech issues: Ask for the common problems and how the vendor’s team solves them.; The implementation dip: Lead the team through the slump in confidence and set up small, early wins.PLANNINGFive rollout pitfallsand how to head them offCommon snags when adopting new technology01Hidden costsAsk for five examples of extra fees,then have the vendor review your fullbudget.02Too few internal resourcesName the roles early and bring theproject owner into vendor talks.03No go-to-market planReview the rollout plan with thevendor and ask what you are missing.04Unexpected tech issuesAsk for the common problems and howthe vendor’s team solves them.05The implementation dipLead the team through the slump inconfidence and set up small, earlywins.Source: Masttro; “implementation dip” from MichaelFullan, Leading in a Culture of Change
"I really appreciate their amazing customer support. The team is attentive and dedicated, and they don't just stop at software implementation. They've been really helpful with different scenarios."
Sabrina B.
Sabrina B.
Family Office Accounting Manager, Austin, TX
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Yes, change can be difficult. But it’s also necessary if you want to remain relevant and grow your organization. By incorporating good communication with the vendor and your team, and some advanced planning, you can prevent many of the roadblocks that often arise so that the implementation process is smooth sailing.

Want to learn how Masttro can support you through this transition? Schedule time with one of our wealth tech experts.

In their words
What clients say about Masttro
“The initial setup was very easy, and the Masttro team was extremely helpful throughout the process. The efficiency we have gained from implementing Masttro in our small firm of 4 employees has been great.”
Sheldon C.
Sheldon C.
Small Business
“Masttro quickly turned out to be much more than a technology vendor... Their business model makes them a true technological partner that supports us proactively in our growth strategy, and in turn has differentiated our value proposition tremendously.”
Maurizio Cereda
Maurizio Cereda
Director, Wealthness
“I think Masttro has been a guide for how we can do better, of how we should organize ourselves. It has helped us understand where we’re standing today so we can look to the future.”
Pola Zaga
Pola Zaga
Director Single Family Office