Ask the Experts: Why Sales Planning Breaks Down Without Alignment

In our Experts in ICM Q&A Series, we’re sitting down with leaders from across the incentive compensation and sales performance management space to explore learnings, trends, and opportunities that exist for today’s ICM and SPM professionals.

In this installment, we examine why sales planning so often fails. And it’s rarely because the math is wrong. More often, it breaks down due to misalignment.

Incentive compensation and sales planning sit at the intersection of finance, sales, HR, operations, and executive leadership. Each group brings its own priorities, constraints, and perspectives. Without clear communication and shared expectations, even a well-designed plan can lose credibility before it ever goes live.

CaptivateIQ CMO Katie Foote is joined by Christopher Goff, Senior Director of Sales Compensation at Labcorp, and Greg Peña, Lead Senior Financial Analyst at BigCommerce, to discuss how planning teams can collaborate more effectively across departments and move forward with confidence, even when plans are imperfect.

From setting expectations early to building feedback loops that strengthen trust, our experts share practical guidance for navigating the messy, collaborative reality of modern sales planning.

Why is sales planning so important? 

Chris: Revenue is the lifeblood of any organization. Practitioners, consultants, and technology — all of these things exist with the intent of helping organizations execute better. 

What’s important to remember is it’s not just about ensuring the sellers can make more money. It’s also about ensuring companies can be successful and continue to employ everyone in the organization. Because without revenue, none of that is possible. 

Katie: It’s the rising tide that lifts all boats. 

Chris: Exactly. 

What’s your biggest piece of advice or learning for compensation professionals in the planning process? 

Chris: One common pitfall is trying to do too much, going too wide or too deep when the organization isn’t ready. We’re always constrained by organizational readiness. The culture at that moment in time, strategic alignment, and other factors all play a role in what’s possible. 

It’s important not to lose sight of where you are in your point of evolution. Once you’re in sync, you can effectively help the organization evolve. This is a game of constant evolution. You’re never really done.

Katie: Every decision you make, from a planning perspective, comes with consequences. If you try to do too much at one time, it can turn into a hornet’s nest very quickly.

Chris: Do what you can, and don’t get caught up in chasing perfection. The reality is you can only move the world so much and so quickly. It’s okay if the plan isn’t exactly what you envisioned right now.

There’s a little bit of personal reflection here. For most of us, we struggle with thinking things should be perfect all the time, even when our reality looks very different. It’s okay. You’re still moving in the right direction.

Katie: When things go poorly, it feels like the end of the world. When things go beautifully, no one says anything. There’s an element of catharsis and group support that’s often missing, but deeply needed.

Greg: Give yourself some grace. You want to make sure your team is confident in operationalizing the plan. 

[BLOCKQUOTE
| Quote: You’re always optimizing and monitoring, and there’s still time to make adjustments as the year progresses.
| Author: Greg Peña
| Title: Lead Senior Financial Analyst, BigCommerce
]

What are the steps that have to be taken to prevent conflict between different stakeholders? 

Chris: I don’t know if you can truly prevent conflict, but you can improve the environment in the room. A lot of that depends on personalities. More often, it comes from establishing a regular cadence of engagement and interaction, which helps build trust around decision-making, ideation, and ongoing modification.

This often shows up in the form of governance. You create a structure that says, we’re going to meet regularly, we’re going to be open and transparent, and we’re going to identify areas for exceptions, adjustments, and regular review. That gives stakeholders a chance to align on what’s being proposed. It’s not a set-it-and-forget-it exercise.

What’s often taken for granted is that planning teams live in this world every day, while the people on the other side of the table only see snapshots of it. Unless we do a better job explaining what we’re trying to establish or improve, and showing that we’re accounting for both the people involved and the organization as a whole, gaps will form.

You’re often walking a fine line between competing priorities. There’s the familiar scenario where sales wants to pay sellers more and finance wants to pay them less. Overcoming that tension requires a trusted environment, where you can negotiate, influence, and align stakeholders around shared goals.

[BLOCKQUOTE
| Quote: In a remote-heavy, digital-heavy world, you have to communicate twice as hard. That means using multiple channels and being consistent. In the absence of communication, people fill in the gaps with their own stories, and that’s where trust starts to break down.
| Author: Katie Foote
| Title: CMO, CaptivateIQ
]

When you’re trying to get leadership teams to buy in on new plans, what’s your go-to strategy?

Greg: The best thing you can do is start with transparency. Make sure leaders understand the core objective of the plan. It helps to remind everyone that you’re all on the same team and working toward the same outcome, incentivizing the right behaviors in the right way.

That means listening closely to leadership concerns before moving forward with a specific plan. Loop leadership in earlier, understand their goals and constraints, and make sure you’re aligned with those priorities from the start.

Katie: Part of your role in building alignment and getting everyone to a place of consensus is recognizing that you’ll need leadership’s support. They’re the ones who help bring others along on that journey, which is why it makes sense to loop them in much earlier in the process.

How do you manage differing opinions? 

Chris: It really starts with understanding what each stakeholder cares about most. From there, you can tailor your message to those interests. For example, if you’re talking to a CFO versus an FP&A analyst you work with regularly, the focus and level of detail will naturally be different.

Sometimes it helps to think about it through a RACI-style lens. You may be informing some stakeholders, while seeking approval or deeper engagement from others. It all depends on how much buy-in is required. The key is customizing both the message and the depth of information to match the audience.

Katie: It’s Marketing 101. Know your audience, and be clear about what’s in it for them.

How should organizations ensure that employees fully understand their plan, especially when changes have been made? 

Chris: This is where sales management really has to own the message. Our role, as compensation professionals, is generally behind the scenes. We tee up the communication for management, make sure the analysis is sound, and ensure we’re not dramatically increasing costs. Then, we hand it off to sales leadership, and they need to be the owners.

We don’t want managers saying, “Well, corporate says XYZ,” because that immediately undermines credibility and creates an us-versus-them dynamic. When that happens, you lose the opportunity for a strong rollout.

It also means communicating in a way that’s understandable and accessible to different levels of experience. One effective approach is clearly explaining what’s changed year over year, whether that’s through plan notes, a deck, or other supporting materials.

Finally, it’s important to think about how people learn. That may mean offering information in multiple formats: written, verbal, video, one-on-one, or group sessions.

Ultimately, people have to understand the plan. If they don’t, it’s a waste of money. 

[BLOCKQUOTE
| Quote: If sellers can’t figure out how to work their plan, both the employee and the company lose.
| Author: Christopher Goff
| Title: Senior Director of Sales Compensation at Labcorp
]

Katie: I’m reminded of the classic mom-and-dad analogy. When a child goes to one parent and hears, “Well, your dad says you have to do this,” it undermines the sense of shared ownership and teamwork.

How do you get the sales leaders excited about the plans and help them transfer that excitement to the organization? 

Greg: Sales leaders play a direct role in shaping the plan. You need early buy-in and collaboration from sales leadership for the plan to be as effective as possible. That collaboration alone starts to build trust and enthusiasm. We don’t want to be the bad guys, and we need partners who can help carry that excitement forward. At the end of the day, we’re excited because we’ve built something we believe can be truly lucrative for reps.

Katie: It’s deeply personal for people. For many, this is their livelihood. It’s what gets them out of bed every day. That’s why it’s important to strike the right balance between what’s working well in the plan and what may be challenging. In a healthy environment, people can voice concerns about the hard parts and receive thoughtful, informed responses.

Creating space for what people may be frustrated or uneasy about is critical, in my experience, while also reinforcing the excitement around the opportunity ahead and why the plan sets the stage for a strong year.

Greg: It also helps to show tangible examples. When leaders can clearly see that doing the right things leads to a great year, it reinforces confidence in the plan and makes the excitement much easier to share.

How do you get buy-in from executives when you’re presenting big changes? 

Chris: One of the things I try to do is talk to the people around that executive to understand how they respond, how they like to consume information, and how they typically react to change. I do as much background preparation as possible, because at that moment, it’s really about the conversation between us.

If I need a hard sign-off, that means doing even more homework upfront so I can use the limited time I have with them as effectively as possible.

Are there key milestones that are critical to avoiding rushed rollouts? 

Greg: It depends on the magnitude of the change. You want to establish clear deadlines for things like which metrics will be used, which teams will be on the plan, and when communications will be finalized and shared with reps. That also includes planning office hours or support sessions.

Having those larger milestones clearly defined helps you manage both the project and your time. If you don’t plan for them, it’s easy to miss important steps. And if you’re winging it, you’re far more likely to miss a key deadline, which makes the rollout less effective than it should be.

How many months should be allocated for implementing a significant change? 

Chris: If you don’t have any historical reference points, you can’t go wrong starting as early as possible. If you do have at least a year of historical data, you probably need a minimum of six months to implement major changes. That said, it also depends on the level of support you have and the specifics of your situation. No matter what, it almost always takes longer than you expect.

When we talk about significant change, there’s buy-in required from sales, but there are also process changes to account for. You have to consider how many processes are involved from an input or data-collection perspective. That means reverse-engineering all known modifications or gating steps, whether that’s milestones, approvals, or spend. You need to do a lot of homework to fully understand what’s required.

<hr>

If you’re interested in participating in one of the Multiplier Q&A features, reach out to us at multiplier@captivateiq.com.