Excellent at the Wrong Thing: Sara Ann Straw on Event ROI, Executive Language, and Why Great Planners Get Passed Over

TL;DR

Most event teams are not badly run. They are badly wired. In this episode of Event About It, Megan Martin sits down with Sara Ann Straw, a global event leader who has spent nearly two decades walking into fractured event organizations and rebuilding them from the inside. The conversation starts with a game and ends somewhere much more uncomfortable: the meeting where a CRO asked why the company was investing in its own event, and Sara’s honest answer was “because I was told to.”

Key Takeaway: Event professionals are not being passed over because they execute poorly. They are being passed over because they cannot speak to what their events produce. Event ROI is a language problem before it is a data problem.

Summary

Sara Ann Straw did not plan a career in events. She trained in motor control design at a technical high school in Buffalo, studied biology and theater management, stage managed musicals in New York, and took an executive assistant job to get out of restaurant work. Two months later her boss asked her to run trade shows. Nearly twenty years on, she runs global event organizations at high-growth technology companies and has just published her first book, The Experienced Executive.

That non-linear path matters, because it is the norm in this industry and nobody prepares for what comes next. Event professionals get hired for execution, promoted for execution, praised for execution, and then watch someone with half their operational experience take the strategy role.

This episode covers:

Why “we’ve always done it this way” is the most expensive line in an event budget
The difference between executor thinking and executive thinking, tested live across ten real scenarios
The four data points executives consistently ask for, and why registration counts are not among them
What happens to a lead that sits longer than 24 hours, and how that fuels the marketing and sales blame cycle
The Strategy, Alignment, Scale framework and what scale actually means
What a fragmented event organization costs, with real numbers attached

From a game called Executor or Executive Move to a sales kickoff that nearly collapsed six weeks out, this one is equal parts diagnostic and confessional. If you are accountable for event outcomes and not just event delivery, this is required listening.

Key Themes & Takeaways

1. Most Event Teams Aren’t Badly Run. They’re Badly Wired.

“I think when things are so separate, you feel like you’re on your own island. You’re almost on a treadmill running to nowhere.”

The Problem: Partner events sit in one place. Webinars sit somewhere else. Field marketing reports into the regions. Corporate events runs its own show. Four teams, four calendars, four definitions of success, and no shared view of what any of it produced.

Sara’s Take: Events should be run as a whole. Corporate events sets the strategy and becomes the center of excellence for how the company shows up in market. Field and digital localize it. Partner events fold in because strategic partner programs carry direct sales, brand, and corporate weight simultaneously. Field teams can still hold a dotted line into their regions, but they need one leader who can advocate upward on their behalf.

Why It Matters for Event Pros: Fragmentation is not just an org chart inconvenience. It is why nobody can answer the ROI question. When four teams each own a slice of the event portfolio, no one owns the number.

Key Takeaway: Before you can prove what your events produce, someone has to be able to see all of them at once.

2. Executor or Executive: The Difference Is the Question You Ask

“Really asking the question why you’re even planning that regional dinner. What is it actually doing for the business? Or do you just want to go to the Cubs game?”

The Game: Megan read out ten real decisions event teams make every week. Sara sorted each into executor thinking or executive thinking in real time. Some were obvious. Several were not.

What separated them: A twelve percent budget increase that nobody can explain is executive territory, because the conversation about where that investment goes has to happen. A forty-slide recap sent the Monday after an event is executor work. A contingency line carried forward five years out of habit is executor thinking, and the executive move is not deleting it but interrogating what has changed. Five years ago contingency meant pivoting to virtual. Now it might mean splitting a conference across two regions because of travel conditions.

The answer that will start an argument: Volunteering for the event nobody else wants is, in Sara’s read, executor behavior. Not because volunteering is bad, but because event people have been conditioned into being the yes team. Executives push back more. That distinction is uncomfortable and it is worth sitting with.

Key Takeaway: Executor and executive are not job levels. They are two different reflexes when a decision lands on your desk. One asks how. The other asks why first.

3. “Because I Was Told To” Is the Most Expensive Sentence in Events

“The first question out of my CRO’s mouth was, can you remind me again why we’re investing in this? And my answer was, well, because I was told to.”

What Happened: Sara walked into what she thought was a routine planning meeting with her CMO and CRO. She brought a binder, a laptop, and a highlighter. She was ready to report registration numbers, food and beverage status, and virtual attendance. Logistical metrics, as she calls them.

The CRO did not want any of that.

What Happened Next: They pulled up Salesforce dashboards live in the room. Customer churn rate. Expansion rate. What percentage of customers were attending. Sara plugged in numbers on the spot. The meeting turned into a strategy session, and by the end the event had an expansion target, a lead generation goal, and eighty million dollars of pipeline expected in the room.

She left with imposter syndrome and a genuine question about whether she should be leading the team.

The Reframe That Changed Everything: Sara had always assumed that conversation was above her pay grade. Then she realized she had been promoted into that pay grade and nobody had told her the job description had changed.

Key Takeaway: The gap between where you were promoted to and what you were trained for is where most event careers stall. Nobody hands you the new job description. You have to go find it.

4. What She Did in the Weeks After Is the Actual Lesson

“I started really digging into what our data said. And asking the questions.”

Getting caught without an answer is not the interesting part. Everyone gets caught eventually. What Sara did next is the repeatable piece:

Weekly alignment calls with marketing operations on lead scoring and routing models, to understand how event data actually reached sales
Direct conversations with sales leadership about full-year goals, not just the slice events were expected to contribute
A seat in the weekly pipeline review, which she asked her CMO for directly even though the room was VP and above
Getting comfortable with definitions, so she understood what she was looking at rather than nodding along

Much of the pipeline call was irrelevant to her week. She kept going anyway, because understanding how the business was performing changed how she planned.

What It Produced: Not a better version of one event. A rebuilt portfolio. Field programs, webinars, digital, and corporate all changed, because she could finally see that the team had been running status quo programs that did not support what sales actually needed.

Key Takeaway: Ask to be in the room before you are qualified to be in it. That is the entire move.

The After Show

5. The Four Numbers Executives Actually Want

“So we have six hundred registrations. What are the logos in the room?”

This is the most portable thing in the entire conversation. When Sara reports to executives now, four data points come with her:

Who is in the room, by account tier. Not the headcount. The named accounts, sorted by strategic importance.
What percentage have open opportunities. Pipeline present in the room, not pipeline attributed afterward.
Which attending accounts are up for renewal in the next six months. These are the rooms where a small, deliberate gesture changes an outcome.
How many attendees are repeats from last year. Return rate is a brand trust signal, especially in a category crowded with competing conferences.

The follow-on question Megan adds: If a repeat attendee is not a customer, what is that signal telling you, and what should sales or marketing do with it? If they are a customer and they keep coming back, what does that say about loyalty that your retention model is not capturing?

How to get these numbers: Go on a listening tour before the meeting. Take the attendee list to the sales team and ask about specific accounts. That conversation gives you the data and it curates the on-site experience at the same time.

Key Takeaway: Attendance is a logistics metric. Account composition is a business metric. Executives were never asking for the first one.

6. Three Flawless Launches and No Promotion

“She did not understand the data. And I know that might sound silly.”

The Story: An event leader ran three flawless product launches. Exceptional project management. Strong relationships across the organization. People spoke highly of her. She spent nearly two years building those relationships deliberately.

She lost the director role to someone with half her operational experience.

Why: In a room with executives, she could not speak to why the launches happened in the first place or what they produced. She knew the basics, that a launch gets a product into market. She could not go further.

What the other candidate did: Ran an analysis comparing product performance in the first six months for launches versus releases without launch support. Brought the difference in adoption rate into the room. Positioned herself around what the work produced rather than how well it was run.

Key Takeaway: It was not personal and it was not politics. Relationships get you considered. Data gets you selected.

7. Strategy, Alignment, Scale

“It’s not just about scale as in can we do a million more events.”

Sara’s framework came out of six or seven notebooks. She had been writing down single lines about things that happened at work, a habit borrowed from writing one-line fragments as a kid and turning them into songs at the end of the month. When she went back through them, every entry marked itself with the same three letters.

Strategy. Why are we doing this, and does it support the actual business goals? For a flagship user conference at a fully remote company, the answer is not only closing sales. It may be that this is the one moment customers are met in person all year.

Alignment. Are the right people involved in the decision? Product wants one thing from a conference. Sales wants another. Brand wants a third. The executive team wants a fourth. Alignment means finding the nucleus, the core reason underneath all of them.

Scale. Can this be delivered consistently and sustainably across the organization? Not more events. Consistency. Sara points to a company that renamed its event every single year, so it built zero recognition and zero trust. Contrast that with Dreamforce, where the name is the asset. Scale is also moving from eighty million in pipeline in the room to a hundred million next year.

The initials are also Sara Ann Straw, which her mentor pointed out and which is now permanently the joke.

Key Takeaway: Scale is consistency compounding, not volume multiplying.

8. Nobody Is Following Up, on Either Side of the Table

“Anything that’s not met within 24 hours usually drops about 33% in conversion rate.”

The Vent, Part One: The push and pull between sales and marketing, and the scapegoating that comes with it. Marketing gets blamed for lead quality. When you look at the leads, they are fine. What actually happened is that service level agreements on first touch were missed, or a lead got touched once and never again.

Sara is direct about accountability running both ways. Are we enabling sales well enough? Are we communicating when leads land? And also: are you touching them?

The Vent, Part Two: Venues and hotel brands fly event professionals in for site visits, then never follow up. Sara mentioned wanting to look at a brand’s venues for the following year while at CEMA Summit. A week and a half later, nothing.

That is a hot lead going cold, from the same industry complaining about hot leads going cold.

Megan’s addition: The same pattern shows up with testimonials, photos, and advisory board feedback. Planners will give it. Almost nobody asks.

Key Takeaway: The industry has a follow-up problem it is only willing to diagnose in other people.

9. Vendor Versus Partner Is a Budget Decision

“I don’t even like the word vendor. I definitely always say partner.”

The Situation: Six weeks out from a two thousand person sales kickoff in Las Vegas. Attendees flying in globally. Then Sara’s leader was cut in a round of layoffs, and the production vendor, loyal to that leader, walked with her.

No production. No keynote. No expo. Six weeks.

What Saved It: A phone call to someone she knew. On a call the next day, in full the day after that. The event ran, and people at that company still describe it as the best sales kickoff they have attended.

The Detail That Matters: Crew was so thin that the head of sales at the partner agency personally worked the keynote door, ushering attendees to their seats.

Key Takeaway: A vendor delivers scope. A partner absorbs risk. The distinction only becomes visible on the worst week of your year, which is exactly when it is too late to build.

10. What a Fragmented Event Org Actually Costs

“Right there we saved a hundred and thirty thousand a year by getting rid of that agency.”

When Sara pulled webinars under her field program, the agency the webinar team had been using for execution was no longer necessary. That was a hundred and thirty thousand dollars a year, from a single structural decision.

The second-order effect was bigger. Field marketers who had only been running field events started running webinars, working with the centralized paid team, and advising on regional paid placement. They stopped being the events people in the market and became actual field marketers.

Key Takeaway: Consolidating an event organization is a cost story and a career development story at the same time. Most teams only pitch the first one.

Final Word

There is a version of this conversation that is about data literacy, and it would be useful and forgettable.

This one is about something harder. Event professionals have spent a generation being rewarded for the thing that is easiest to see, which is flawless delivery, and then being quietly excluded from the conversation about what any of it was for. Nobody taught this. Hospitality programs do not teach it. The associations largely do not teach it. Most people learn it the way Sara did, which is in a meeting, in front of a CRO, going red to the tips of their ears.

The fix is not another certification. It is asking to be in the pipeline review before anyone thinks you belong there.

Key Takeaway: Stop being excellent at the wrong thing. The work you are already doing produces business outcomes. Learn the language those outcomes are discussed in, and the ceiling you have been assuming was structural turns out to have been a vocabulary problem.

Frequently Asked Questions

What four numbers do executives want from an event?

Executives consistently ask for four things: which accounts are in the room and at what tier, what percentage of attendees have open opportunities, which attending accounts are up for renewal in the next six months, and how many attendees are returning from the prior year. Together these convert an attendance report into first-party event data that maps to revenue, retention, and expansion.

Why do executives ask about pipeline instead of registration numbers?

Registration is a logistics metric. It confirms an event happened at the expected size. Pipeline in the room tells leadership what revenue exposure the investment created. A conference with six hundred attendees and twenty million dollars of mid-market pipeline is a fundamentally different investment than one with six hundred attendees and eighty million in enterprise pipeline, even though the registration number is identical.

What is the difference between executor thinking and executive thinking in events?

Executor thinking starts with how: how do we deliver this, on time, on budget, to standard. Executive thinking starts with why: what business outcome is this serving, and is this the right investment to produce it. Both are necessary and organizations need people doing both. The mistake is assuming that excellence at the first automatically qualifies you for the second.

Why do great event planners get passed over for strategic roles?

Not because of execution quality or relationships. In the case discussed in this episode, an event leader with three flawless product launches lost a director role to someone with half her operational experience, because she could not speak to what those launches produced in business terms. Relationships get a candidate considered. The ability to speak to outcomes is what gets them selected.

What is the Strategy, Alignment, Scale framework?

Strategy, Alignment, Scale is a decision framework developed by event leader Sara Ann Straw and detailed in her book The Experienced Executive. Strategy asks why an initiative is being run and whether it supports business goals. Alignment asks whether the right teams are involved and whether there is a shared definition of success. Scale asks whether the program can be delivered consistently and sustainably across the organization, which means consistency compounding over time rather than simply running more events.

How fast does an event lead lose value if nobody follows up?

Leads that are not touched within the first 24 business hours typically drop about 33 percent in conversion rate. This is why service level agreements on first touch matter more than lead volume, and why the recurring argument about lead quality between marketing and sales is often actually an argument about follow-up speed.

What is the difference between an event vendor and an event partner?

A vendor delivers a defined scope of work. A partner operates as an extension of the team and shares accountability for the outcome. The difference is invisible when everything goes to plan and decisive when it does not, as in the case discussed here where a production partner rebuilt a two thousand person sales kickoff on six weeks notice after the original vendor walked.

Should field marketing, webinars, and partner events sit under one event leader?

There is a legitimate argument for field marketing reporting into field organizations, since it aligns directly to regional sales goals. The counter-argument made in this episode is that events should run as a whole, with corporate events setting strategy as a center of excellence and regional teams localizing it. Consolidation creates coverage across the team, negotiating leverage, a single view of the portfolio, and in one case documented here, a hundred and thirty thousand dollars in annual agency savings.

How do event professionals learn to speak executive language?

Not primarily through formal education. The approach described in this episode: request a seat in weekly pipeline review meetings even when the room is more senior, hold regular alignment calls with marketing operations on lead scoring and routing, learn the definitions behind the dashboards rather than nodding along, and ask sales leadership what the full-year goals are rather than only the events contribution.

Listen & Subscribe

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Connect with Sara Ann Straw:

Website: saraannstraw.com
Book: The Experienced Executive — https://a.co/d/07Rit5wG
Podcast: Solo Travel Woman, on Spotify
LinkedIn: https://www.linkedin.com/in/saras23/

Connect with Megan Martin:

Podcast: EventAboutItPodcast.com
Newsletter (Step and Repeat): msquareddynamics.com/stepandrepeatsignup
Consulting and strategy: msquareddynamics.com
LinkedIn: https://www.linkedin.com/in/meganmartincmp/
Instagram: @m2dynamics and @eventaboutit
TikTok: @eventaboutit

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