The Most Costly Stakeholder Management Mistakes in Enablement 

Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.

Introduction

I’ve spent a lot of time exploring what works in stakeholder management (in enablement).

Most recently, in my article on best practices, I gathered the hard-won wisdom of enablement leaders from across the industry.

But as many in enablement know, success isn’t just about having a list of best practices; it’s about learning how to avoid the common pitfalls that may derail your effort along the way. 

Because to get stakeholder management right, you need more than a playbook of what to do. 

You also need a clear view of what NOT to do – the missteps that quietly erode trust, alignment, and forward progress.

That’s why, after exploring what effective stakeholder collaboration looks like, I went back to the same enablement leaders – this time to surface the patterns, blind spots, and mistakes they’ve made in their careers, and they see most often, even in seasoned teams.

The contributors include: 

Alex Bedford – GTM Enablement Lead

Alicia Heagle – Revenue Enablement Lead

Christopher Kingman – VP of Sales Transformation

Darwin Singson – Revenue Enablement Lead

Dave Turis – Director of Sales Enablement

Dawn O’Rourke – Senior Director, Revenue Enablement

Georgia Watson – Enablement Leader, Australia & New Zealand

Giorgia Ortiz – Senior Director, Global Revenue Enablement

Jill Guardia – Senior Vice President, Revenue Enablement & Operations

Lisa Hammack – Director, Global Field Enablement

Meganne Brezina – Head of Enablement

Sam Moody – Global Director of GTM and CS Enablement

Sam Wener – Senior Director, Sales Enablement

Samantha Thompson – Director, Global Sales Enablement

Sheryl Buscheck – Director, Global Revenue Enablement

Timea Bara – VP, GTM Enablement

Umar Gill – Vice President, Commercial Enablement

Their responses were candid, sometimes a bit too real, but always instructive. 

They reveal that most mistakes aren’t the result of laziness or lack of care. 

More often, they come from good intentions: wanting to be helpful, moving too fast, or assuming alignment that isn’t really there.

In the sections that follow, you’ll find the most common stakeholder missteps, as seen by the people who’ve experienced them firsthand.

Each theme is paired with practical advice for spotting these pitfalls early – and, more importantly, for building habits that help you avoid them altogether. 

If you’ve ever found yourself wondering why a well-planned initiative fizzled or why a promising stakeholder partnership lost steam, you’re in the right place.

Let’s get honest about what goes wrong so we can all get better at what matters most!

Stakeholder management mistakes – common themes

For the purposes of easier reading, I’ve organised the responses from my contributors into themes which capture the patterns and pitfalls that surfaced most often. 

Each one reflects the real world and provides a chance to improve how we build and sustain stakeholder partnerships.

Failing to grasp what matters most to stakeholders

It’s easy to treat stakeholders as a checklist – names to update, approvals to gather, boxes to tick. 

Real partnership, though, starts with seeing things from their side: their goals, pressures, and day-to-day realities.

Christopher Kingman, the VP of Sales Transformation at the world’s leading consumer intelligence company, has seen what happens when enablement leaders treat stakeholders as project managers or decision-makers, rather than partners who need guidance and leadership:

“Asking too much of stakeholders – Stakeholders are called that for a reason. They are holding the proverbial structure up. 

They are not necessarily there to do the work, make all the decisions, and guide the efforts. 

It’s been my experience, and where I’ve had the most success, that stakeholders want guidance and leadership, and want to be informed and consulted when necessary. 

In my experience, your initiative is just one of many they need to balance, so the more you handle the planning, tracking, communicating, and majority decision making, the more trust and support you gain.

If your stakeholders feel like they need to do your job, it will inhibit your future efforts to launch additional programs and impact your perception as a leader.”

Failing to understand stakeholder expectations, goals and motivations, or making them feel like outsiders, leads to disengagement and missed opportunities for buy-in, as Darwin Singson, the Revenue Enablement Lead at a pioneer in global pay transparency solutions, points out.

The understanding of stakeholders also extends to how you communicate with them. 

Timea Bara, the VP of GTM Enablement at a leading legal ediscovery software company, highlights a common pitfall: not tailoring your message to the audience, whether it’s C-level leadership or a project team of some kind. 

She’s seen how communicating at the wrong level (too much detail for some, not enough for others) can leave stakeholders disengaged or confused:

“Not knowing their audience – communicating at levels that are not adequate to the stakeholder. I.e. VP+ will be interested in a very different level of information from field managers.

Crafting your message accordingly – i.e. including exec summaries with key points on the problem and solutions suggested, before diving into details.”

There’s also the risk of pushing ahead with enablement initiatives without relating them to what stakeholders actually do every day. 

Umar Gill, the Vice President of Commercial Enablement at a global leader in industrial software, makes it clear that every interaction needs to tie back to the realities of the stakeholder’s role:

“Leading with their work without alignment to the realities that the stakeholder faces. 

Every interaction must somehow be related to the day job, and understanding that is a skill every enabler needs. 

Selling a programme of work to an internal (or external) stakeholder interests is a key part of enablement’s role.”

My contributors agree – the most effective enablement professionals start with curiosity and empathy, asking, listening, and adapting to ensure that every initiative feels relevant and every stakeholder feels seen and understood.

Not involving stakeholders enough

Understanding your stakeholders is only the first step. 

The next, and equally vital, move is to actively involve them throughout the process. 

Too often, enablement professionals treat stakeholder engagement as a box to tick at the start of a project, rather than an ongoing partnership. 

When stakeholders aren’t included in shaping, vetting, and approving initiatives, they’re left feeling like outsiders, not true members of the team.

Darwin Singson highlights all the ways in which enablers sometimes drop the ball:

“Not having them vet what you are creating or the program you want to launch. 

Not having them agree and approve it. 

Not having them feel they are a member of the team for this project. 

They should not feel like just a stakeholder but a member of the team.”

Georgia Watson, the Enablement Leader for Australia & New Zealand at one of the world’s biggest tech companies, takes this idea further, emphasising the need for long-term allies rather than transactional relationships:

“Like our sellers with deals, enablers need to build long-term partner allies—not just stakeholders. 

We need people who speak for us when we’re not in the room, who share honest feedback, and who co-create for high-impact enablement.”

Involvement also entails bringing stakeholders along for the journey. Sam Wener points out the danger of assuming stakeholders know the problem you’re trying to solve, instead of starting with the “why” and co-creating solutions:

“Not leading with the problem you’re trying to solve for. In other words, assuming your stakeholders know what the problem is vs. bringing them along on the journey by telling—always start with the ‘why.’”

When you involve stakeholders as true partners (inviting their input, validating your approach, and co-creating solutions), you build deeper buy-in, uncover blind spots early, and set the stage for sustainable, high-impact enablement. 

Moreover, you turn stakeholders into champions for your work.

Saying yes to everything

It’s a natural impulse in enablement: you want to be seen as helpful, responsive, and indispensable. So, when a stakeholder comes with a request, the easiest answer is “yes.” 

But that reflex can quickly spiral into chaos – overcommitting your team, diluting your impact, and eroding trust with the very people you’re trying to support.

Samantha Thompson, the Director of Global Sales Enablement at a cybersec platform, has seen the fallout from this pattern:

“The most common mistake I see enablers make when managing stakeholders is defaulting to ‘Yes’ as soon as the request is presented as opposed to saying ‘Interesting, let me think about that.’ 

This results in ‘random acts of enablement’, makes the team less focused / unaligned to key programs, and can lead to burnout.

In short, the compounding effects can be catastrophic to the entire enablement function. 

There’s nothing unkind or uncooperative about asking for space to think through the request; it shows that you’re a thoughtful, strategic partner.”

The desire to help is understandable, but without boundaries and clear alignment, it can turn enablement into a bottomless hole where requests go in and little of value comes out. 

Meganne Brezina, the Head of Enablement at a leading enterprise SaaS Management platform, warns about what happens when you say yes to everything without guardrails:

“Enablers say ‘yes’ too often. 

It usually comes from a good place—we want to be helpful, prove our value, and move fast. 

But when we say yes to everything without guardrails, we become a black box where projects go in… and often don’t come out the other side. 

That erodes trust and makes it harder for stakeholders to see enablement as a strategic partner.

Instead, I believe in being vocal and transparent about what we take on and why. 

That means clearly articulating how an initiative aligns to business objectives, defining milestones and success metrics up front, and regularly reporting progress, blockers, and pivots to the right stakeholders. 

When we operate with clarity and accountability, we not only protect our own capacity—we elevate enablement as a high-performing, business-driving function.”

Lisa Hammack, the Director of Global Field Enablement at an API-first analytics platform, adds that enablement teams often jump at every request without taking the time to understand the business outcome, which leads to reactive work and missed priorities:

“I think they are reactive and jump at every request without taking the time to understand the business outcome that the stakeholder is looking to achieve.”

Lisa also provides a suggestion on how to prevent this mistake:

“Here, we start with an intake form that includes detailed information about the request, and if bandwidth is impacted, we aren’t afraid to say no or to ask them to help us re-prioritize projects.”

Saying yes to everything might feel like the path of least resistance, but it’s a fast track to burnout and strategic irrelevance.

The most effective enablement leaders pause, clarify, and commit only to what truly moves the business forward.

Not being strategic

Saying yes to every request is often where a lack of strategic focus begins, but it is definitely not where it stops. 

This is something I’ve personally seen happen with many enablement functions – they approach what they do without any high-level strategy, which makes it nearly impossible to be truly effective. 

Sheryl Buscheck, the Director of Global Revenue Enablement at a network infrastructure leader, provides the perfect segue from the previous section:

“I think the worst thing you can do is become an ‘order taker’ – waiting for requests and reacting to them rather than strategizing how you can contribute to business goals. 

This results in ‘random acts of Enablement’ and one-off programs that may or may not have any long-term value. 

You’ll end up overwhelmed with tasks and won’t be able to prove your value to the organization.”

Alex Bedford, the GTM Enablement Lead at a leading enterprise microsegmentation company, highlights other strategic mistakes, such as the risks of aligning too closely with a single leader or function, and renouncing the ownership of metrics and decision rights:

“Aligning with only one leader/function without capturing metrics and not holding ‘final edit’ rights on any content pushed to sellers. 

Enablers need to more consultative in their approach and have the confidence to push back/question/ get to the root cause of requests…even from senior leaders (e.g. ‘we need to train xxx sellers on xxx product using yyyy methodology’ will likely not yield the results intended).”

Dawn O’Rourke, the Senior Director of Revenue Enablement at a platform for intelligent connectivity and automation, points out that strategy also means tailoring your approach as blanket enablement rarely delivers results:

“Another mistake is blanket enablement — assuming one size fits all. 

Foundational learning is important, but it’s equally critical to meet teams where they are. Tailor your programs to address performance gaps by role, segment, or region. 

What your enterprise sellers need may be very different from what your commercial reps need this quarter. The key is to stay flexible, data-informed, and stakeholder-led, not just content-driven.”

Sam Moody, the Global Director of GTM and CS Enablement at a company behind one of the most popular HR platforms, reminds us that enablement events and activities are only part of the equation. 

Strategic enablement means connecting the dots between learning and the business’s greater goals:

“A common mistake I see enablers make is focusing too much on the success of a learning event, instead of creating a learning environment that connects to the bigger picture (like business initiatives and OKRs). 

Events definitely matter and they have their place, but they’re just part of the equation. 

The real impact comes from building a continuous learning culture that aligns with the business’s greater goals. 

I approach this by working with key stakeholders to design a series of post-event activities that stretch over multiple months or quarters, if needed. 

These might include practice labs, team meeting exercises, AI-based role plays, and manager coaching rubrics. From there, I team up with RevOps and VPs to identify performance criteria, and then those specific folks are required to engage with some mix of the follow-up work.”

Being strategic entails questioning, prioritising, and designing enablement that truly moves the business forward.

When you step out of reactive mode and into a consultative, data-driven partnership, enablement becomes a driver of long-term value, not just a service desk for ad-hoc requests.

Assuming too much, communicating too little

Whenever I hear or see the word assumption, I remember this scene from Lock, Stock and Two Smoking Barrels:

(Warning: the video contains strong language.) 

And while the wording from the excerpt may be a bit too strong, the fact remains that assumptions can derail even the finest, most thought-out enablement programmes and interventions. 

And this is particularly relevant when it comes to stakeholder management.

Dawn O’Rourke, for instance, spells out the risk of assuming alignment on priorities, and she directly links prevention to the kind of stakeholder involvement discussed in the previous section:

“One of the most common mistakes I see is assuming there’s alignment on priorities without confirming it. 

This leads to enablement initiatives that may be well-executed but ultimately miss the mark because they’re not solving for the most pressing business needs.

Instead, I recommend over-communicating early and often — don’t just share plans, co-create them. 

Use 1:1s with sales leaders to validate what matters most for the business that quarter, and ensure enablement is focused on directly impacting those goals.”

Giorgia Ortiz, the Senior Director of Global Revenue Enablement at the biggest equity management software company, is even more direct about the dangers of assumption in stakeholder management:

“Assumptions. Assuming anything when it comes to stakeholders is a fool’s errand. 

Discovery is one of the core selling skills every enablement program focuses on and it is the central skill every Enablement professional must master. 

Being truly curious and testing assumptions will avoid miscommunications and program irrelevance.”

Timea Bara highlights another common pitfall: assuming awareness. 

She points out that just because you’ve discussed an initiative, it doesn’t mean it’s top of mind for your stakeholders:

“It is very common for enablement to assume that because we discussed an initiative, it’s top of mind for GTM leads. 

However, there is always a lot going on and we need to constantly keep the conversation going in order to ensure there is awareness.”

Alicia Heagle brings it back to the basics of expectation-setting, showing how easy it is to assume alignment just because something has been communicated once:

“A common mistake I see enablers make is not setting clear expectations early on. It’s easy to assume that once you’ve communicated your enablement plan, everyone is aligned, but often, that’s not the case. 

Misalignment happens when stakeholders aren’t clear on what’s expected of them, what success looks like, and how they’re being supported.

I always try to be proactive and transparent: I clarify roles, timelines, and goals/outcomes upfront. 

I also know that emails and Slack messages get missed, so I prioritize constant communication and reminders (though, to be honest, this is always a challenge!). 

A lot of this role is really about project management, keeping everyone aligned, managing moving pieces, and ensuring follow-ups don’t fall through the cracks. 

I’m always working on improving that communication flow with my stakeholders.”

Assumptions are the silent killers of alignment and impact. The best enablement professionals replace assumption with curiosity, confirmation, and constant communication, never leaving alignment to chance.

Treating stakeholder alignment as a one-off event

It’s tempting to treat stakeholder alignment as a milestone to check off: a single meeting, a signed-off plan, or a kick-off call. 

But successful stakeholder management is never a one-and-done event. 

Without ongoing engagement, even the best-laid plans drift off course, and initial buy-in fades as priorities shift and new challenges emerge.

Dave Turis, the Director of Sales Enablement for US at a world-famous Japanese company, sees this mistake often:

“I see this time and time again, treating stakeholder engagement as a one-time event rather than an ongoing relationship.”

Dave also shares his framework for preventing this from happening:

“I treat stakeholder management as a continuous, strategic partnership. 

I schedule regular touchpoints and check-ins (every Friday at 9 am, I meet with our corporate vice president of sales)—not just for updates, but to listen, gather stakeholder feedback, and adapt. 

I also use data and storytelling to keep stakeholders engaged, showing how enablement is driving tangible outcomes. 

This ongoing dialogue builds trust, keeps initiatives aligned with business priorities, and ensures long-term support.”

Jill Guardia, the Senior Vice President of Revenue Enablement & Operations at one of the world’s leading digital learning companies, highlights the danger of assuming early agreement equals lasting buy-in, and the importance of building in checkpoints and measurement throughout the lifecycle of an initiative:

“One common mistake is thinking one alignment discussion is complete buy-in. 

The programs you are running evolve as they are rolled out. It’s important to build in checkpoints with project stakeholders, understand if any of the objectives and goals have changed, as well as content and measure at different milestones to ensure the outcome is going to deliver against the agreed-upon plan. 

I would spend time up front building in critical success factors, metrics and KPIs and calendar time to keep those lines of communication open.”

Darwin Singson recommends weekly check-in meetings with the stakeholders.

Effective stakeholder management requires more than a strong start. The most effective enablement leaders treat stakeholder relationships as living partnerships, anchored by regular check-ins, open feedback, and a shared commitment to adapt as the business evolves. 

Conclusion

Mistakes in stakeholder management aren’t necessarily a sign of carelessness or poor effort. 

They’re a sign you’re in the arena, doing the real work. 

Every leader I spoke to for this article has stumbled at some point, sometimes in ways that stung. 

But, as Rocky Balboa says in Rocky VI: 

“It ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward.”

That’s what sets the best apart – not perfection, but resilience, reflection, and the will to keep building stronger partnerships.

If there’s one thing these stories make clear, it’s that the most costly mistakes often come from good intentions: trying to help, moving fast, wanting to please. 

So, if you recognise your own missteps in these pages, you’re in good company. 

Use them as a springboard. 

Pause, check your assumptions, hone your stakeholder management skills, involve your stakeholders early and often, and never let alignment become a one-off event. 

That’s how you turn honest mistakes into lasting progress and how you make stakeholder management and alignment a genuine source of impact. 

Finally, another huge thanks to Alex, Alicia, Christopher, Darwin, Dave, Dawn, Georgia, Giorgia, Jill, Lisa, Meganne, Sam Moody, Sam Wener, Samantha, Sheryl, Timea, and Umar, for making this piece possible.