Jun 10, 2022

Read Time 5 min

The five biggest Customer Success software implementation mistakes—and how to avoid them


Implementing a Customer Success platform is a momentous occasion—the mark of a new beginning and growth. But it can also be an intimidating undertaking, especially for first-time buyers.

You must take inventory of all your data points and sources, get your operations in order, and corral internal stakeholders for support. There are many moving parts that make it prone to miscommunications and mistakes without a well-defined project goal, plan, and owner.

As an implementation team lead, I’ve overseen hundreds of launches—the good, the bad, and the ugly. I know the ins and outs of what makes an implementation a success as well as the warning signs that you’re headed for trouble. Avoid these five common implementation mistakes to keep your project on track, on time, and on budget.

1. Not securing internal stakeholder commitment

You may feel the urge to ask for forgiveness, not permission when it comes to securing stakeholder buy-in. Better to act swiftly and keep the momentum going than bother with the rep tape, right? While this outlook may hold true in other areas of business, software implementation is not one of them.

By far the biggest impediment to this process is a lack of internal commitment.

Conduct your due diligence during the sales process before you purchase. Identify the required levels of stakeholder backing. Who needs to be informed? Who needs to be included in decisions? Who needs to give final approval? Get quantified and explicitly agreed-upon commitments from each party to support the implementation, preferably in writing.

Once the implementation is underway, make sure to follow through with assigned homework or action items. Hold your team accountable to the same standards as you would your vendor.

2. Allocating insufficient resources to execute

Another common yet avoidable downfall is underestimating or not scoping the organizational resources and time needed to complete implementation.

I see this roadblock occur most often when CS teams need internal development resources to assist with their implementation. SaaS product teams often plan their roadmaps at least a year in advance. It’s unreasonable to spring a surprise project on your team and expect them to delay their priority work.

Make a list of every data point you plan to integrate. Share it with your vendor during the sales process and ask for an approximate implementation timeline. Your sales rep should be able to tell you how long and involved your implementation will be based on these details. Then, brief the owners of the data points on those requirements and expectations to ensure they’re prepped for what’s to come. Be specific. Spell it out. Never assume others know what a step or process involves. It’s always better to overcommunicate than under-communicate during times of decision and change.

It’s also important to note that the internal support for implementing a CS platform will widely vary depending on your product, team structure, and use case. For instance, pulling in a developer to build an API integration to connect your product to a CS platform is a much more involved task than tapping a CRM admin to identify key fields to include in a native CRM integration. Just like the scope for importing a handful of usage events looks very different from importing 50+ usage events.

All that said, an implementation should not be a full-time job, but it does need time and attention to be rolled out successfully. Plan accordingly.

3. Not nominating a project manager or champion

A big project—like CS platform implementation—that has multiple stakeholders (i.e., opportunities for crossed wires) needs defined ownership. Who is ultimately responsible for the success of your implementation? Assign one project manager or champion to bear that accountability. Otherwise, the responsibility will fall to everyone, which as we know, is the same as falling to no one.

A project manager will also help decrease inconsistencies and inefficiencies. This role serves as the main point of contact for your vendor’s implementation team. All vendor communications funnel through the project manager who then distributes relevant messaging and tasks to the wider team, and vice versa.

In addition to acting as a gatekeeper, a good project manager does two things: they assign responsibilities and set due dates. You should be able to point to any aspect of the project and know who owns it and its timeline for completion.

Once ownership is delegated and dates are set, establish communication guidelines with your vendor or internal team to ensure they’re upheld. In other words, if a team member misses a deadline, how should they be held accountable? For example, do you want the project owner or vendor to notify the individual’s supervisor, set a follow-up meeting to discuss the implications, or send a notice to the group that the project plan shifted due to their delay? Discuss how you want to hold your team, including its leaders, to their deadlines, so they realize that the work of others depends on them completing their part on time.

4. Having an inconsistent meeting schedule

You and your vendor should walk away from every implementation meeting knowing when your next touchpoint will be. A recurring structure raises project visibility and therefore accountability.

I recommend setting a weekly or bi-weekly meeting cadence. If you don’t want to commit to a timetable, then aim to schedule the next call before you leave the current call. That way, tasks remain top of mind and get allocated time since they’re always associated with a defined future date. For example, a team member should leave a meeting knowing they have from now until next week (or whenever your next meeting is scheduled for) to complete these five specific tasks.

When deliverables aren’t routinely monitored, they tend to inadvertently fall down the list of priorities.

5. Hiding concerns

Keeping your worries to yourself only makes them accumulate and grow. If for whatever reason you don’t feel like you’re getting what you need, voice those concerns. Expressing your thoughts helps alleviate pent-up tension and move toward a solution. Even when practicing careful listening, it can be hard for your implementation specialist, or anyone, to read between the lines. Be open and give honest feedback. It’s one of the best ways to strengthen the partnership with your vendor and build confidence on both sides.

And remember to trust the implementation team. They have seen this process many times and are keenly attuned to the nuances, consequences, and reasoning behind each step. Take advantage of their expertise. Use them as a trusted guide. And never be afraid to ask questions or for help. That’s exactly what they’re there for.

Do the upfront work for long-term software success

There are no shortcuts in software implementation. It’s hard work but it’s work that’s every bit worth doing. To walk away with a CS platform that seamlessly integrates into your team’s operations—so you’re no longer bogged down by workarounds, spreadsheets, and multiple systems—is what CS dreams are made of. You’ll never regret the time you invest to clean up and map your data. You’ll be stronger for it in the end as will your team’s insights and value to the organization.

Now that you know what mistakes to watch out for, the next step is to see if you’re ready for a CS platform implementation. Learn the steps you can take right now to prepare with our Customer Success software implementation readiness checklist.


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