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Transforming How Product Teams Work

Difficult Customer Conversations
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Applying research from the Harvard Negotiation Project


Despite best efforts to delight customers, everyone on a product team eventually needs to tackle a difficult conversation with a customer – whether they expect it or not.

Without knowing how to handle customer conflict, your team risks escalating a misunderstanding and missing an opportunity to learn from, and deepen their relationship with, your most important customers.


In every company, it’s inevitable that you inadvertently – and, some might argue, even periodically - create an angry customer despite your best efforts. At the root of customer conflict is mismatched expectations, such as a product not behaving as expected or over-promising and under-delivering on customer commitments. You may be temped to believe a customer is “difficult” by their nature, or see your company as poorly executing a well-established process. The reality, however, is that most often angry customers are the result of trade-offs that organizations make – whether decided appropriately or not. These might include shifting resources from one product to another, prioritizing enhancements for one customer segment over another, or judging when product quality is sufficient to release. Given that product management, at its core, is about leading an organization through intelligent trade-off decision-making, product teams can expect to encounter an unhappy customer eventually.

Of course, the types of situations in which angry customers are encountered vary widely. Some we expect, such as when we investigate a recurring pattern of support cases that are escalated to, or perhaps discovered by, a product team. Then there are the ones – my favorites – which we don’t expect, such as when we are caught off guard during:

·         Conversations with customers related to a business case

·         Interviews with customers about product requirements

·         Feedback sessions on the product roadmap

·         Research on user personas or use scenarios

·         Evaluation of customer retention strategies

Learning how to best handle these scenarios is a critical skill for product teams to develop, as the risks in mishandling them are significant. There’s always the potential of accidentally escalating the conflict or mis-setting expectations even further – which could come back to haunt your organization at contract renewal. In social media conversations, or even during trade shows, an unresolved conflict can get amplified to dissuade new prospects from purchasing. Perhaps most importantly, though, is the missed opportunity for your product team to learn from the customer’s perspective, advocate internally with it, and deepen the team’s relationship with key customer accounts. To many buyers, the way a vendor handles an escalated problem is just as important as how it realizes the value it promised all along.

In their bestselling book Difficult Conversations – How to Discuss What Matters Most, Douglas Stone, Bruce Patton, and Sheila Heen of the Harvard Negotiation Project (HNP) present some best practices in how to handle difficult interpersonal conversations – which I adapt here to apply to customer conversations. The HNP, founded in 1981 at Harvard Law School, is comprised of many of the world’s leading scholars of negotiation theory and practice.

If you’re lucky enough to be able to anticipate a conversation with an unhappy customer, it’s always critical to get as much context as you can beforehand from internal sources. How important is this customer to the business? Is this a reference account, or a relatively large account? Is a renewal looming on the horizon, which could be used as leverage by the customer during the conversation? Is there a history of frustration on the part of the customer? Are they representative of a target segment – or more of an outlier? Speak to the account manager and invite them to participate in each difficult conversation you anticipate.

Whether anticipated or not, when your customer conversation goes south, it’s important to be aware of the 2 distinct phases of the conversation: problem discovery and problem solving. Each requires dedicating some time, and each calls for using different skills and achieving different ends. While this sounds obvious, many product managers’ natural inclination is jump into problem solving too early out of a desire to avoid or minimize conflict. This can leave customers with the feeling of not being heard or the impact of the issue not being appreciated. Often, this results in a residual anger or unhappiness that awaits the next accident to explode anew.

Problem Discovery

During problem discovery, your primary goal should be to listen actively and explore impact. Darden Business School at the University of Virginia has a terrific technical note on active listening, written by Professor James Clawson. As he explains, most of the time when we listen we do so passively – simply paying attention to the content of the other person without interaction. During active listening, we seek to hear the person on multiple levels, and we reflect back what we hear to ensure both that we understood correctly and also so that the customer can “see” it clearly. This helps other people feel heard, and can serve as a powerful tool for communicating empathy and building trust in the process.

During active listening, the 4 key skills to practice are:

·         Suspending judgment. Momentarily set aside any judgments or beliefs about what may be right or wrong – and just listen to understand. This can be hard for some – particularly those who mistakenly believe that not taking an immediate position will be interpreted as implicitly taking responsibility or committing to doing what the customer wants. At this point, we are still exploring the issue and it’s impact on the customer.

·         Focusing on emotion as well as content. Our natural inclination with customers is to ignore emotions during tense moments and focus on problem solving. After all, focusing on problem solving seems easier than talking about feelings or emotions. However, unexpressed feelings can accumulate and burst into a present or future conversation without warning. Moreover, unexpressed feelings can inhibit a customer’s ability to listen to you when it’s your turn to speak, and leave them with a sense of not being truly heard. Emotions reflect the intensity of a person’s thoughts and experience, so acknowledge what you perceive while demonstrating empathy using phrases like, “I hear how upset you are” or “I can understand why that would be confusing”.

·         Following, not leading, the conversation. The goal during active listening is to give the customer complete freedom to pursue issues and topics of their choosing. This helps the customer express all facets of the issue and begin to feel heard.

·         Reflecting accurately what you hear. Test that you’ve understood correctly what the customer is saying, and show them that you heard, by asking questions and paraphrasing what you hear as you follow the conversation. Examples might include: “Just so I understand, you’re saying that...”, or “If I heard you correctly, the impact was …”.

While active listening is a key technique to use during problem discovery, it’s important to know what to listen for when you use it. As Stone, Patten, and Heen point out, every difficult conversation is really about 3 conversations:

·         The “what happened?” conversation. First and foremost, listen for the sequence of events that led to the issue from the customer’s perspective. What was observed and what did the customer conclude? Map contributing causes by determining what contributed to the undesirable outcome both from the customer’s end, as well as your company’s end. What was the impact on the customer organization? You may need to suspend active listening and ask a few open-ended questions to find out.

·         The feelings conversation. Listen carefully for feelings, as sometimes determining the customer’s emotional state can be difficult. Anger and fear may be obvious, but picking up on ambivalence, confusion, or a vague uneasiness can be subtle. Use the feelings expressed as an internal measure of the perceived intensity of the issue.

·         The identity conversation. Listen for any personal concerns that your customer contact has – and, in particular, ones that relate to their identity within the organization. These might include unarticulated or implied fears that they or their organization might be abandoned or unsupported by you. As a result of this issue, are they concerned about how they will look to their colleagues, to senior management, or to other stakeholders of the purchase? Acknowledge this directly, and use this opportunity to appreciate any championing of your product that your customer contact has demonstrated internally. Examples might include: “I appreciate how much you’ve championed the rollout of our product over the last year, and I hear how this issue has put you in an awkward position with department heads.”

Once you’ve given the customer a chance to fully express their concerns, and you understand the impact of the issue on their organization and on themselves personally, it’s now time to switch to problem solving.

Problem Solving

During problem solving, your primary goal should be to take the lead and advocate internally for the customer. This is a more natural phase than problem discovery for most product management teams, as it leverages the same problem solving skills that are used for requirements research. The difference here, of course, is that the communications with the customer need to be more carefully managed.

Here are 7 guidelines you can follow as you lead the customer through this phase:

·         Acknowledge failures. During problem discovery, it was critical to suspend judgment to more fully explore the customer’s experience of the issue. Now it’s time to bring it back. Turning back to your map of contributing causes during the “what happened?” conversation, which if these did your organization create? Acknowledge failures where they occurred, and present some visibility into your organization to explain how they occurred. Organizations grow and mature over time just like people, so paint a picture of what stage of maturity yours is at. Being real and honest is an important step towards re-establishing a sense of trust with the customer.

·         Gather solution requirements. Research what would be required to rectify the situation – and, in some cases, the customer relationship. You can ask the customer directly with a question like, “what would be needed to resolve this situation? Why?” Some requirements may be hard, such as restoring a broken product capability, while others may be softer, such as restoring a sense of trust in you.

·         Advocate internally and explore options. In between customer conversations, pull together a cross-functional team with the account manager and lead the team in exploring options that address the issue. Be a champion for the customer’s needs, and communicate what you learned during problem discovery. This is where your findings from the 3 conversations (on what happened and the impact to feelings and identity) are critical to bringing the team up to speed and creating a complete picture.

·         Present choices. Encourage the cross-functional team to identify multiple options with which to present the customer. Prefer options that put a trade-off decision in the customer’s hands. For example, let’s say that the customer uncovered a major defect in your software product that is moderately impacting their organization, and that there is a heavy customer cost (perhaps testing & validation) to upgrading to a new version. You might offer to trade-off the time to a fix with the work required to deploy it: either wait 1 month for a major release that will fix the issue, or upgrade now to a patch and then upgrade again to the major release in 1 month. Presenting a choice will help the customer to regain a sense of control, and will also maximize the likelihood they buy-in to the solution afterwards - since they participated in choosing it.

·         Re-set expectations. Be up-front with the customer about where you are in the process and what they can expect. Provide visibility into how your organization makes decisions and how you are advocating internally on their behalf. If their expectations for a resolution aren’t going to fly internally, explain this as early as possible. You can buy more time to “see what I can do internally” if needed.

·         Balance bad news with good. If you need to deliver bad news, and if the relationship warrants it, get internal buy-in for some token of goodwill you can extend to the customer. This might include giving away a product or service for free, or possibly extending a renewal date at no cost. Even a small gift can go a long way - such as a fruit basket or chocolates sent to your customer contact along with a letter explaining remedial steps you’ve taken to avoid recurrence of the issue.

·         Over-communicate along the way. During problem solving, resolution, and follow-up, seek to communicate more regularly than normal with the customer to show you are on top of the situation. For a pressing issue at a key customer site, at least a daily touchpoint (either by phone or email) is a good goal. Encourage your customer contact to email or call you in the interim of they have any concerns. Making yourself available will demonstrate that you are committed to a resolution and will help to restore the customer relationship.

Problem discovery and problem solving are complementary phases of tackling any difficult customer conversation. Problem discovery is about active listening and exploration, while problem solving is about taking action and advocating. Of course, each situation may call for a different amount of time spent in each phase. However, slowing down to give the customer an opportunity to feel heard (even if only briefly) before taking action will help you learn from your customers, strengthen your relationship with them, and, paradoxically, address issues more quickly when they arise.

Jonathan Levene is a Boston-based executive coach specializing in leadership development of product management executives and directors. He is a 14-year veteran of product development organizations in small and mid-size companies and a former president of the Boston Product Management Association. Jonathan offers tools and evidence-based training and coaching programs on leading effective change management initiatives, influencing leaders in other functions, and developing product teams for peak performance. For articles and tools on product leadership, visit

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