10 biggest challenges of customer success (& solutions)

Every customer success team shares a common goal: to make customers happy. But as any customer success professional knows, that’s easier said than done.

To dig deeper into how teams can crack the customer happiness code, we held a live webinar, 8 simple rules for making customers happy. We ended with a Q&A, where more than 200 customer success professionals shared their most pressing customer success challenges. Heads of Customer Success at Front and Guru, Sarah Sheikh and Hillary Curran, talked through their solutions for each one.

Customer success challenges & solutions

1. How do you empower your teams to invest in customer relationships with accounts that have multiple contacts, especially when new contacts or stakeholders are introduced?

Front: You won’t always know when a new person joins the customer’s team. Try your best to monitor big changes at the executive level in those companies via the news. Then reach out proactively to figure out how you can engage with that new leader. It's hard to do at scale, but building out a customer org chart can help you stay up to date with their team structure.

Guru: One of the first things we try to do with our champions is figure out who their boss and their boss's boss is, and then determine what those people care about. If you want to empower your customers to show value internally, you need to know what "value" means to different stakeholders.

2. What is the best way to manage the passover to a new team member post-sale that doesn't bring unease to the customer?

Guru: We try to make sure that the sales-to-CS handoff conversation takes place before the sale is even finalized, and we often bring CS team members into the final phases of a deal so that the prospect can meet who will be managing their account.

In terms of account transitions internally, when handing an account off from one CS team member to another, we try to make that transition as smooth as possible with a standardized template. We aim to do it in person and give the customer fun facts about their new CSM so they can get to know them and feel comfortable with them quickly.

Front: Our team wrote about a few tips for the handoff from Sales to Customer Success in the past. First, explain the breakdown between people, and who’s responsible for what. If customers will interact with a salesperson, an implementation specialist, and then a customer success manager within their first 90 days, walk them through those different phases. Be upfront about when those transitions will occur. Customers will feel more comfortable if you show that you’re a tight-knit team that’s constantly in sync — so your customers won’t have to worry about miscommunications between your team.

3. How do you keep company morale up around the office when things are busy or tough?

Front: Don't sugarcoat things. If there is a down time in the organization, acknowledge it! You hired these people because they want to be there and are able handle the truth. If there is an elephant in the room, acknowledge it and share the plan to remove it.

Guru: That, and shine a light on people who are working hard. Let the rest of the team know that a certain person has accomplished something. We share new customer success wins with the entire company to give some credit to our CX teams after successful implementations.

4. What is the top metric for your team?

Guru: The #1 thing for our success team is adoption of the Guru product. We want to see the entire team that has access to Guru actually engaging with it and finding value in the product. This is a quick determinant to see if an account needs more love or another nudge.

Front: We know that there are critical Front features that deliver success, so we look closely at which features accounts use. We also look at how often they're on the platform and how they're engaging with it.

5. How scalable is the concept of speaking the customer's language? Can you really support dozens, hundreds, thousands of clients in this way?

Front: This is certainly a challenging part about being a customer success manager and leading a customer success team. Scaling this is possible with two key actions: 1) being diligent with your note-taking and 2) keeping a robust, always-updated database of customer information. Whether this is your CMS, or something homegrown for your customer success team, you need a place where your customer information can live, and everyone can update it as you hold conversations.

Our small customer success team at Front supports all our customers this way. We built our customer database into our inboxes using Front's API, so all of our customer information is available next to every message. We also use Front’s comments feature to leave context on email threads. For instance, “This customer will be out of office, reply in March.” That way, you remember what was happening when you come back to the message, and if a teammate needs to jump in and answer, they also have the context the need to reply.

Guru: We use Guru much in the same way. Because the browser extension overlays any window, we can add quick facts about every client into Guru and have those available when we’re communicating with them over email, Zoom, or Slack. As Sarah mentioned, keeping diligent notes from client calls is immensely important, but saving those notes some place where anyone can access them is also extremely important. That way, even if any given CSM has a large list of clients to take care of and no time to memorize the specific terminology or naming conventions each one uses, they can reference that saved information on the fly for a quick refresher.

6. Often, clients will only provide feedback when they believe they're being listened to. When they stop providing feedback because they feel it's useless, how do you re-engage them?

Front: Honesty is a great conversational hook. Re-engage customers by being honest with them. Let them know that you realize it’s probably frustrating to feel like they’re not being heard. If you need to apologize, go ahead and own up to it. Then, don’t dwell on it. Jump right in to your goals and how you’re going to move forward. A great way to re-engage customers is to just show you appreciate them, like with snail mail, or sending a quick “hello” video from your team. With something a little more creative than your average email, they’re more likely to respond and continue to give feedback.

Last, the best way to let them know that their feedback isn’t useless, is to close the loop. When you deliver on something, like fixing a bug or releasing a new feature, let them know! Send them a personal email thanking them for their idea, their patience, and letting them know their wish has been granted. (Our team did a fun example of video shoutouts last holiday season.)

Guru: Agreed, setting the expectation upfront that all feedback is valuable, no matter if it's good or bad, is key. At Guru, we are super diligent about following up with customers when their feedback is incorporated into our product in someway — be it a new shiny feature, updated design, or small adjustment to a workflow — it is critical that our customers know their comments had an impact.

On the flip side, when a customer suggests or requests something that we know will not fit into our product roadmap any time soon, we are extremely transparent and honest about that, too! If you set unrealistic expectations, and your product does not evolve in the way you suggested to your customer, it makes them feel like their feedback is useless. This will prevent customers from providing feedback in the future, which can be detrimental to your company’s growth. TLDR: Be transparent about what’s coming up next and what isn’t. Your customers will value your honesty.

7. What is the single greatest advantage to using the Guru integration with Front, versus a dedicated Guru browser tab?

Front: We love using these apps — so we wrote an entire article on the benefits we’ve seen from having Front and Guru internally. From our perspective, there are two major benefits of integrating the two tools.

  • 1. You have access to all your Guru information, directly in your inbox. This saves your team time because you’re not switching back and forth between tabs to find what you need. Switching tabs makes you likely to get distracted (check out the costs of context switching), and every second you spend pulling open another page is time you could be spending with customers.

  • 2. Your information stays up-to-date. A huge problem with internal knowledge bases is that as soon as someone finds wrong information, they lose all trust in it. They’re likely to stop using it. The Front Guru integration makes this much less likely to happen, because your Front Admins can edit and update Guru information directly in their inboxes. The minute something changes, it can be edited and reflected for everyone on the team.

8. What's your take on having all members of the company shadow the support organization to stay in sync with customers?

Front: This is extremely important to our culture at Front. We constantly have opportunities for the entire team to jump into the support queue and help out. For instance, after our weekly All Hands, we hold Customer Care Workshops where anyone can spend time answering requests, or learning how to answer support questions from the support team. We incorporate a Customer Care Workshop into every company offsite, and we emphasize to every new hire that it’s important to learn what questions customers are asking about our product.

Allowing anyone to help with support is easy since we use Front. We have shared support inboxes that the whole team can access, so anyone from any team can jump in and help out at any time. This also keeps our team close to customer needs, even if they’re not actively on the phone with them everyday.

Guru: I love this idea! While we have yet to emulate this at Guru, we have plans to do so later this year by making a “Day in Support” a part of new-hire onboarding. Giving all employees real-life experience answering customer questions is extremely valuable as they not only learn about our customer’s needs, but also learn how to quickly search for up to date information in Guru to answer any and all questions.

9. Do you have any advice on segmenting the responsibilities of the sales, success, and support functions, so autonomy lines and collaboration can be clearer?

Guru: At Guru, we like to think of our sales, success, and support teams as components of one larger Revenue Team, since we all share a common goal of delighting customers and driving revenue. By organizing our customer-facing teams under one umbrella, we promote communication across the organization and are able to help those teams ensure a smooth experience for all customers, regardless of the stage of the funnel.

When those teams do act separately, we document clear handoff processes in Guru so that everyone can access them on the fly. There are Guru cards to facilitate the account transition from account development rep to account executive and from account executive to CSM. That way there’s no confusion as to which team should handle certain interactions.

10. How do you use your office space to share positive and negative customer feedback? Any ideas to help the Customer Support and Success teams to stay motivated and inspired?

Front: Physically displaying positive and negative feedback is huge! If you have TV screens or dashboards in your office, try loading your customers’ comments there one day a week. If you have a company meeting or All Hands, save a 5-minute segment to read a few positive and negative NPS comments aloud. Make a bulletin board and split it down the middle: one side is for positive feedback, one is for negative. Encourage the entire team to print out comments and post there. This is great because it gets everyone accustomed to talking about and sharing the negative — which is just as important, if not more so, than the positive.

Guru: Our CX team is split between our Philadelphia and San Francisco offices, so we like to use Slack to share feedback, success stories, and words of encouragement. We have channels dedicated to product feedback, notable CS wins, customer questions, and even channels dedicated to specific clients so all teams interacting with that client can share feedback and motivation.

We also use a software called 15five to monitor performance and engagement on a weekly basis. 15Five has this cool feature called High Fives, which allows any team member to give props to someone else for something they did that week. At the end of the week, all High Fives are automatically routed to a Slack feed for the entire company to see and react to. Being able to publicly thank someone who made a difference in your week or call attention to someone going above and beyond promotes positive reinforcement within CS and across the company.

And finally, when we are together in person at events like Town Halls, there are always opportunities to shout out team members who have been living our core values. Town Halls serve as a great forum to share the remarkable work our CS team is doing on a much larger scale.

Solving tough customer success challenges

No matter what challenge you're up against, remind your team: We're all humans! Being helpful, thoughtful, and understanding when interacting with your customers can be the keys to unlocking customer success.

10 customer success challenges and solutions - HubSpot,Shopify, Countsy