Revenue Builders · 24 Sep 2026 · From the week of 21 September
Why Your Reps Leave SKOs No Better Equipped to Sell with John McMahon and John Kaplan
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Hosts John McMahon, a five-time CRO, and John Kaplan, co-founder of Force Management, discuss how to plan a sales kickoff (SKO) that changes what reps do the Monday after. They argue that most SKOs mix too much inspiration with too little execution and try to cram around 30 topics into two or three days, so reps leave without knowing what to change. Their main point is to pick two or three things the sales force needs to do better, tie them to deal outcomes, and train managers as well as reps.
For founders
- Kaplan said product messaging should be tested with the best sellers before the SKO, because a senior seller's questions can make a product or campaign fall flat in the room.
- McMahon said product sessions should cover the persona, the problem, how the customer measures it and why they should change now, not only what the product does.
- McMahon said an SKO should focus on two or three things the sales force needs to do better rather than trying to cover around 30 topics.
For revenue leaders
- McMahon and Kaplan said managers need their own training at the SKO, because rep training is lost and behaviour will not change unless frontline managers change too.
- McMahon said the SKO should answer what a rep does differently on Monday, based on what leaders see across the sales force about where reps get stalled in deals.
- Kaplan said reps should practise building business cases during the SKO rather than only hearing about them, building on McMahon's point that companies do not teach reps enough about business cases.
- McMahon said late comp plans and territory assignments leave reps sitting on their hands for up to a month after year end, and that these should be delivered before the SKO.
- McMahon said CROs should get out from behind their desk and ride along on sales calls to learn what is really happening in the organisation.
What was said 17, most useful first
Build the SKO around what a rep should do differently on Monday, based on where the CRO sees reps getting stalled in deals. Listen
McMahon said the SKO should answer what a rep needs to do on Monday, based on what you see across your sales force about where reps get stalled in deals and the two or three areas behind it. He said reps do not care about executives on stage or the org chart, only how the company will help and train them to do their job more effectively.
“Je moet de vraag over wat ik als rep moet doen in Monday.”
Cramming around 30 topics into a two or three day SKO means reps retain almost none of them, so train on only two or three things. Listen
McMahon said companies try to squeeze a full year of content into two or three days, covering product, the new price, compensation, messaging, mid-market, prospecting, AI, CRM hygiene and process. He said this leaves the agenda overrun, and he advised picking two or three things the sales force really needs and training only on those.
“they jam the agenda with 30 things of which no one's going to be able to retain 30 things.”
Product sessions at an SKO should explain the persona, the problem, how the customer measures it and why they should change now. Listen
McMahon said product managers often present new demos and roadmaps without answering these questions, and reps sit there with no idea what is being said, so the whole hour is lost. He said reps care about how the product solves their customers' problems rather than what it does.
“Because they don't care what the product does. They only care about how it solves problems for their customer, who's the persona we're selling it to?”
Test product and messaging claims with the best sellers before the SKO, because a senior seller's questions can make a campaign fall flat in the room. Listen
Kaplan said that if product people have not tested their messaging with the company's best sellers and gathered feedback, the sellers will raise the gaps in the room. He said nothing is worse than a product, strategy or campaign falling flat because a senior seller asks questions the team cannot answer.
“And if you don't have answers for that, like if your a product person and you haven't tested that with some of the best sellers in the company”
Managers need their own track at the SKO, because behaviour change for sellers will not happen unless frontline managers change too. Listen
McMahon said SKOs rarely separate rep, manager and executive training, that managers need to learn to inspect deals, coach, challenge reps and customers and qualify, and that training 500 reps is wasted if 50 to 70 managers do not know how to run follow-through. Kaplan added that most companies train everyone together on a new value proposition, product or tool and never address what managers must change.
“In order for that behavioral change to happen it's never going to happen unless something has changed at the frontline sales manager level”
Listen to the episode Sales team, hiring & comp Link to this
Disconnected sales tools force reps to re-enter deal data, which McMahon estimated at about five hours a week of lost selling time. Listen
McMahon described reps juggling Gong, Outreach, Clari, the CRM, Word and Excel, where a Friday update is outdated by Monday. He added that managers and others ask for deal updates after each call, so he estimated three to four weeks of a quarter lost to updating the stack and updating people. Kaplan added that the typical stack is 12 to 15 products that do not talk to each other.
“So where the big productivity losses are is when I gotta update the entire tech stack all the time so I'm wasting probably five hours a week updating the tech stack”
An SKO that adds inspiration and breadth without execution leaves reps with no clear answer on what to do differently. Listen
McMahon said most SKOs he has attended include a CEO review of last year, a motivational speaker unrelated to selling, product announcements and awards, so reps leave energised but with nothing that changes their deals. He said the test is whether reps can say what they will do differently on Monday.
“For me like most SKOs I've attended when I'm not running it myself. It's like too much inspiration and not enough execution, you know?”
A SKO should break a vision down into the strategy to reach it and the specific execution expected of reps. Listen
Kaplan described a sequence: first paint a picture of what great could look like, then make clear the strategy to get there, then state the execution expectation attached to it, and said many people get it wrong. McMahon replied that there is often a big disconnect between the vision and what the rep will do tomorrow.
“First you gotta paint a picture of what great could look like.”
Companies often avoid honest competitive differentiation at SKOs, so reps struggle to defend it to customers. Listen
McMahon said reps want to believe their company's strengths and weaknesses versus competitors, but companies wait for product marketing to supply the message. Reps then repeat those words to customers and later feel the pitch was not said truthfully.
“they're not honest about competitive differentiation which is just so tough on the sales reps because they want to believe”
Reps need to practise building business cases during the SKO, not just hear about them. Listen
McMahon said companies do not spend enough time teaching reps to build business cases covering the cost of the current state, future state value, ROI, payback, risk reduction and strategic impact. Kaplan added that reps are told about it but not given practice, with a lot of telling and little showing and observing, and McMahon agreed that SKOs are usually one-to-many with no real interaction.
“They could do a great job of telling him about it but they don't let him practice it so there's not enough practice”
Late comp plans and territory assignments leave reps sitting on their hands for weeks, so they should be settled before the SKO. Listen
McMahon said CROs are late getting out comp plans and territories: the year ends January 31, reps know their territories have changed but have no comp plan, and the SKO may not happen until March 1, leaving reps sitting on their hands for a month and hurting productivity. Kaplan added that about 50% of the people they talk with have not done this by the SKO.
“No, I don't disagree with one of the biggest issues I see too is that CROs are really late in getting out Komplans en territories.”
Listen to the episode Sales team, hiring & comp Link to this
An SKO should have a specific point on how AI will make sellers more productive, not a general mention of AI. Listen
Kaplan said an SKO should have a point of view on how AI helps sellers do better, be more productive, earn more and help customers, and called an SKO without this a kiss of death. McMahon said that at the highest level the goal is to make sales reps more productive.
“I mean at the highest level that you're gonna make your sales reps more productive.”
Managers who do not trust CRM data end up chasing reps for updates, which replaces coaching with forecast chasing. Listen
McMahon said managers hound and pound reps for updates because they need an accurate forecast and do not trust the data in the tech stack. He said managers should instead go on sales calls with reps and coach them to be more productive.
“They are basically doing what I call chasing the forecast Instead of effectively coaching Going on sales calls with reps and making them more productive”
Listen to the episode Sales team, hiring & comp Link to this
When productivity stalls, the usual CFO levers of cutting SDRs, cutting comp or changing the manager-to-rep ratio do not raise productivity. Listen
McMahon described a CFO pressing a CRO when ramp times rise from about six to nine months and productivity is flat, offering three levers: cut the number of SDRs, cut the comp plan, or change the manager-to-rep ratio. He said these cut cost but do not raise productivity and in fact hurt it further, because the underlying problem is that nobody is training and coaching reps effectively.
“1, we kunnen de nummer van SDR's kopen.”
CROs should get out from behind their desk and ride along on sales calls, because that is how they learn what is really happening. Listen
McMahon said very few companies do this kind of windshield time with reps. Riding in the car, asking what is going on and having meals and drinks with reps lets them hear what is happening in the organisation, some of which they already know and some of which surprises them.
“Get out from behind your desk and get on an airplane, go make some sales calls.”
A CRO can gauge how connected they are to the organisation by whether they recognise reps who have been there a year. Listen
Kaplan said he used a barometer: he asks someone how long they have been there, and if they say a year and he does not know who they are, that is a problem, depending on the size of the organisation. He said this gets harder as the company keeps growing.
“I always use that as a barometer when I'd sit down and be like”
Ask the best sellers to present what they do at the SKO, rather than rewarding them with a bonus, so others can learn from them. Listen
Kaplan said the SKO should feature top sellers not by giving them a big bonus but by asking them and giving them a platform to talk about what they do differently that makes them great, recalling McMahon's advice to let people see what great looks like. He said he wants data on what the best sellers are doing.
“I want data on what the Best Sellers is doing.”
Listen to the episode Sales team, hiring & comp Link to this