Imagine a tightrope walker rhythmically stepping forward, each measured tread steady and progressive.

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That finesse—balancing poise with precision—is the essence of navigating difficult conversations with internal partners. 

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Despite not gliding across a literal rope, these high-stakes talks with sales or other cross-functional partners require a similar level of dexterity. They are delicate dances around ego, expectations, and collaboration, which, if done correctly, can strengthen partnerships and catalyze growth.

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But how do you approach these discussions so they lead to positive outcomes?

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In my 10 years of experience in presales, I was known for how I built up my working relationship with my sales team and made difficult conversations effective and relatively painless. I’ll walk you through my six learnings and share how you can apply them in your work.

1. Building Rapport Through Common Ground

Finding common ground is like discovering a secret handshake. It’s a mutual understanding that says, “I see you, I respect you, and we have shared interests.” As presales professionals, building rapport isn’t optional; it’s required. Before diving into the thick of deal strategies or debating over which product is the right fit with sales teams, invest time in nurturing those relationships.

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Putting it into action: Next time you meet with a cross-functional partner, start the conversation with a compliment or an acknowledgment of their effort. A simple “I’ve noticed the hard work you’ve been putting into X, and it’s really paying off,” can work wonders. This way, in the future, when thorny conversations need to be had, that rapport will act as a cushion, ensuring that disagreements are approached constructively.

2. Understanding Their Context, Explaining Yours

It’s crucial to step into your internal partner’s shoes—be it someone from sales, engineering, or support— to appreciate their perspective. The person you’re talking to has directives from their boss, expectations of presales partners, and personal goals. Approaching a partnership without acknowledging each of those will create endless friction and hinder your ability to accomplish goals. We will have a hard time being successful without the support of our sales partners.

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Putting it into action: When you have a conflicting perspective on what is the best path forward, be curious. Ask your cross-functional partner to unpack their thinking. As they explain their rationale, ask follow-up questions when a logical jump is made and something is being left unsaid. 

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After hearing them out, and be sure to hear them out entirely, here’s a handy phrase I’ve used countless times to great effect, "I understand why you came to that conclusion, but this is how I came to mine…," It acknowledges your counterparty's thought process, ensuring that they know they’ve been heard, before introducing your own perspective. 

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This is particularly effective when discussing product limitations with salespeople, who may face pressure to deliver solutions to clients. Presenting your position with transparency and understanding can foster constructive dialogue that leads to creative solutions.

3. Assume Positive Intent

It is vital to start every working relationship with the assumption that everyone is working towards the same goal and does not have ill intent. Nobody wakes up in the morning with the ambition to make someone else’s life difficult. Maintaining this mindset grounds the reality that you’re working together against a shared challenge versus against the other party, which creates an environment where you can have a productive and honest dialogue.

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Putting it into action: This doesn't mean you overlook mistakes or avoid addressing issues; you simply approach them from a place of cooperative problem-solving rather than accusation. This can make the difference between a simple misunderstanding and a permanent weight on an integral relationship.

4. Learn to Disagree Agreeably

The art of disagreement is not just in ‘what’ you say but ‘how’ you say it. It’s perfectly okay—you may even say, essential—to have differing opinions. But how we express these contrasts can either build or burn bridges. The choice of words matters, the tone carries weight, and timing is everything.

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Putting it into action: Practice phrases like, “I see your point, but have you considered…?” or “Let’s explore a different angle together,” to open up a dialogue that is enriching rather than divisive. Your goal is to ensure the group makes the best decision, not to win or lose the conversation.

5. Preparing the Conversation Framework

When it’s time to have those crucial discussions, preparation is key. Good framework starts with setting a clear agenda. Be upfront about the conversation's purpose. It helps to outline the main points you wish to discuss and keep the discussion on track. It is ideal of you’ve already discussed how you both like to receive feedback.

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Putting it into action: Invite your partner to speak first with suggestions or feedback, this allows for greater trust and empathy when it’s time for you to share your thoughts. When it is your time to discuss, employ the 'FEEL, FELT, FOUND' technique—"I understand how you could FEEL that way; others have FELT similarly, but what we've FOUND is...". This technique acknowledges feelings, validates past experiences, and gently leads the way to a new understanding.

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Moreover, if emotions run high, it’s not a sign to back off but instead an indicator to proceed with even greater care. Empathy here is your comrade. Show that you empathize with their feelings, reiterating that their concerns are valid and heard.

6. Celebrate Wins Together

Finally, make it a team effort.  Recognizing and valuing each other's contributions reinforces positive outcomes and makes future tough talks less daunting.

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Putting it into action: When a project is successful or an impasse is overcome through these difficult conversations, celebrate together by first acknowledging the challenge you both overcame. Even if your partner’s contribution was minimal, letting them know you saw their part in it is impactful. Then celebrate the result! Share a high-five, a toast, or just some kind words.

Putting it all Together

I've seen the following dilemma numerous times when working with complex enterprises. The prospect will need a specific feature or capability that our product simply does not have in its current state. All while the sales team needs this deal for their numbers. This puts us in a difficult scenario.

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In these high-pressure situations, I've found some strategies incredibly effective. First, take time to truly understand the salesperson's challenges and empathize with the pressure they face to close the deal. Make it clear you are aligned in wanting the prospect to ultimately be successful. Next, tactfully explain the limitations in our current product that prevent us from matching the prospect's needs exactly. Outline the specifics on capabilities, roadmap timelines, and any engineering constraints. Be transparent about the trade-offs.

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With both sides understanding the challenges, you can have an open discussion on potential workarounds or alternative solutions. Loop in other stakeholders like product managers to explore options. The salesperson may reach out to their own stakeholders or team members to strategize possible solutions.

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Approaching this collaboratively rather than adversarially is key. With some creative thinking, you may find an acceptable solution that gets the prospect's critical needs met while keeping solutions aligned with our goals.

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Now the prospect has more reasonable expectations on capabilities and timelines. The salesperson sees you as an ally rather than a roadblock. Working together and leveraging each person's expertise leads to a deal that benefits all parties. And you build greater trust and teamwork to celebrate the hard-won success.

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In navigating these tricky discussions, it's the careful balance of assertiveness and empathy, the blended harmony of mutual goals and individual insights, that pave the way for constructive outcomes. By finding common ground with your internal partners, understanding contexts, assuming positive intent, and learning the fine art of agreeable disagreement, you set the stage for a work environment enriched with effective communication and collaboration.

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If you found this post helpful, I’d recommend exploring PSC’s Foundations program where we cover topics like these in depth, practice live simulations, so we can approach similar conversations with confidence in the future, and connect students with world-class presales mentors.