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Sales Offsite and Planning Sessions: A Step by Step Guide

Hosting your company’s sales leadership offsite for the first time can be overwhelming and more than a little intimidating. As the head of sales, you don’t just get to talk about last fiscal period’s wins. You’ll also need to prepare your team for some big challenges and talk about real failures. 

As you begin planning your offsite agenda, be clear on what you, the company, and your team really need to get out of this event. There are 4 main priorities to keep in mind: 

  1. Alignment on the business: Address the success rate of past goals and communicate what needs to happen this year. 
  2. Alignment on the people: What worked–or didn’t work–for your reps last year and what is your people strategy this year. 
  3. Facilitate the sharing of best practices: Tips on winning more deals but also people management
  4. Identify 2 to 4 big bet opportunities: Pinpoint what your leadership team will focus on in the coming financial period. 

→ Here is an agenda template to keep you honest ←

When’s the right time to hold your offsite? 

Plan to host your sales leadership offsite before your general sales kickoff. This gives your leadership team the chance to hone your messaging ahead of time. Regardless if you have sales kickoffs annually or every six months, you should always have a leadership offsite right before. 

While your leadership offsite should happen before the sales kickoff, it must also be after the company executive planning offsite. This way, you have the broader organization goals, usually 3 to 5 initiatives, and the data you need to inform the agenda of your sales leadership offsite. 

These initiatives won’t all touch on the sales organization but as a leader, you need to understand where the company is going and what part sales will play. For example, your goals may need to go beyond simply hitting targets. They could also include improving the revenue mix of renewals and new business or optimizing certain marketing channels. 

Sales leaders need to understand and be able to communicate to their teams WHY these company initiatives have been chosen, especially if some initiatives conflict with their own sales goals. Use the offsite to give your team the clarity they need to move forward. 

Your junior managers have probably never been through this type of planning session before so give them a heads up beforehand so they know what to expect at the offsite. Encourage your managers to take this opportunity to engage with the strategy sessions, especially if they are eyeing a sales director role in the future. 

Always proud and never satisfied

In my experience as a Head of Sales, I found that the right approach to viewing your leadership offsite is to acknowledge your successes, but push for more, or in other words - Always Proud and Never Satisfied.

Start by discussing at least 5 things that worked very well since the last offsite. There are always wins to celebrate and good practices that we should continue to do. But as salespeople, we should never be satisfied. Take time to review the things that didn’t go well. Perhaps your close rates have dropped or you were understaffed at the manager level which affected your success. 

To help with brainstorming, share the OKRs (objectives and key results) from your offsite ahead of time. Then, conduct a 10 to 15-minute postmortem for each OKR. Talk about the high level good and bad, as well as what happened tactically on the sales floor. Over the course of an hour, get everyone on the same page about what went well and what needs improvement. 


Last offsite OKR: To have 5 out of 6 months be above budget on new business revenue.

The results: Only achieved 3 out of 6 months above budget on new business revenue.

Unpack this with your sales leadership team. What happened here? Perhaps you fell short on your SDR hiring plan which affected your top-of-funnel efforts plus threw off your SDR to AE ratio. Ultimately, you just couldn’t get enough leads qualified at the top of the funnel to fill the pipeline. 

Analyzing last year’s successes and failures

Dive into 4 or 5 strategic, northstar questions about everything we just discussed. Then take about an hour to go through the answers to these questions as a team. 

Here are a few questions to ask about how your company missed budget goals due to staffing issues: 

  1. Why are we missing on staffing? And what can we do about it? 
  2. We seem to be slowing down on the ability to bring in renewals to the funnel, how can we increase our top-of-funnel activities for renewals? 
  3. We are seeing that the best reps in the company have the highest number of opps in the closing stage at any time. How can we raise the floor for the rest of the company? 
  4. We have a culture where reps work really hard, but sometimes not really smart. How can we pair these two qualities together? 

You just went through 3 hours of intense goal setting and communication. It’s time to take a break for lunch. Everyone should eat together to talk through what they learned and spend time forming bonds between teams. 

There’s one caveat though. Whoever is the Keeper of the Offsite, usually the VP of Sales, can’t join for lunch because they’re responsible for taking the information from previous sessions and building it into the following sessions as the day progresses. If this is you, you’ll need to use your lunchtime, and a few other breaks during the day, to synthesize all of the new information. 

Your next session of the day is going to focus on helping your team understand what the company is trying to accomplish in the coming 6 months or year. They’ll also brainstorm new goals that are aligned with the company initiatives. 


This session should take around an hour. Start with asking each person to write down 5 executable opportunities they see for the sales organization over the next year on post-it notes. 

The Keeper of the Offsite calls on people to share their ideas and stick their post-it notes onto a whiteboard. Try to group the notes together so you can see which types of ideas are the most popular or top of mind for your leadership team. 

Review your board together. Maybe you have a ton of post-it notes on how focusing on renewals is a big opportunity for the sales team this year. You also see quite a few post-it notes about fixing the hiring process. 

Take all of these ideas, add them to a spreadsheet, and tally up the number of people who support each idea. Moving forward, deciding how to build these goals into an operating plan is not a consensus exercise. As the Keeper, you’ll verify which goals align with the broader company initiatives and come back to the team later in the day with the ones that you determined to be a good fit. 

→ Here is an example deck ←

Tackling your people strategy

You just completed the business component of the sales leadership offsite. Now it’s time to move into the people component. The Keeper of the Offsite will take notes during the following exercise and incorporate this data into upcoming sales goals. This will be a hard conversation to have about your sales reps, so when you’re done with this session, give everyone a break.

Exercise: situational mapping

Each manager will plot their reps on an axis of motivation and skill. Reps will fit into one of these 4 quadrants: 

  1. Low motivation, low skill 
  2. High motivation, low skill 
  3. Low motivation, high skill 
  4. High motivation, high skill 

The Keeper of the Offsite will drive the conversation around each of these 4 personas with a focus on how to care for them. They’ll also review the reps that fall into the high motivation, high skill bucket and identify what makes them successful. What do they do differently? Where are we finding these people? 

I call the reps with low motivation but high skill “breathers.” They might have been a top rep and ranked as high motivation, high skill during the last offsite but now, they’re burned out and need a breather from the grind. For these reps, motivational speeches aren’t going to make a dent. It’s time to give them a paid vacation to rest up and recharge. 

The high motivation but low skill bucket of reps will need to be micromanaged a bit more with a focus on coaching and upskilling. The low motivation, low-skill reps are going to be a difficult conversation. First, find out if there’s any hope here. Why are they in this category? It might be that they were a mis-hire from the beginning. 

Remember, this isn’t a plan to fire people. It’s an exercise to determine the current state of your sales force. You may find that, because of aggressive hiring over the last few months, a whopping 70% of your team is feeling highly motivated but has a low skill level. The answer here may be to focus on sales enablement so you can move as many reps as you can into the high motivation, high skill bucket.  

Don’t just assume that your high motivation, high-skill reps are fine just because they’re top of the pack. If 40% of your reps fit into this bucket but there’s no promotion path in place yet, you risk losing your best people. Focus on how to retain these people.

Best practices sharing

Your next session will be for managers to share what’s working really well for them and their teams and their own unique approaches. The Keeper should choose 3 managers ahead of time to present for 30 minutes each. Make sure you bring up different managers for each sales offsite. 


The Keeper will address each manager about their strengths and ask them to share how they achieve these results. 

“John, compared to other managers, you’re great at managing Gen Z employees. Please show us how you approach these sales reps.” 

“Jane, you really know how to get reps bought into the company strategy. How do you accomplish this?” 

“Jill, your reps’ pipelines are way cleaner than other teams. How do you manage forecasting and sales hygiene?” 

This is a chance for managers to step back from the weeds and share processes that work for them with the greater team. It also accomplishes another equally important goal–helping managers develop respect for each other and their strengths. 

During your final hour of the day, open up the meeting to be more freestyle and reflection oriented. The Keeper needs to keep the focus on getting the main message across to the team. In the past, I’ve talked about how I felt we needed a set of guiding principles as a sales management team to make decisions or make real changes to certain parts of our funnel.

This is your very last session for the day. Ask everyone to share one or two reflections they found most important from the day. Save 10 minutes at the end for a short presentation where the Keeper offers a note of gratitude on a slide for each individual leader at the offsite. This concludes the sales leadership offsite and planning session. 

Dinner and feedback

From here, take everyone out to dinner together. This should be fun with good food and drinks but also include a feedback exercise. I like to practice the Start, Stop, Continue approach created by Patrick Lencioni, an expert in work team dynamics. Each person needs to come up with feedback for every other person in the room.


Tommy, you need to: 

  • Start managing your calendar better - you keep rescheduling my 1/1 meetings.
  • Stop advocating for your reps when you know they are breaking rules. 
  • Continue taking the time to coach your new reps through their first few deals

The goal is to habituate everyone in the room to hearing critical feedback. It’s going to be hard for people who haven’t been through this exercise before. But it will bring your team closer together. Peer feedback is far more compelling. If someone seems to get the same feedback over and over, it will really hit home in a way that a manager can’t get across on their own. 

Creating your charter and operating plan 

At the end of the night, the Keeper should thank everyone for being there and contributing to the planning session. You now have two critical next steps: 

  1. Develop the narrative for the next financial period: Explain what your sales team will be doing, how you screwed up last time, and how your new plan will fix it. This will become the charter that you come back to throughout the year. Since it’s based on the conversations you had today, everyone should be in agreement. Your charter is now set in stone.  
  2. Next, turn your narrative into an operating plan: If the charter is to fix the hiring process in the next 6 months, assign one of your sales leaders to take charge and come up with 7-10 tactics to meet this initiative. Encourage ownership of these strategies and a feedback loop so you can hone the tactics. Do this for each initiative or goal that was determined in your narrative. 

The charter is set in stone but that doesn’t mean that you don’t revisit your operating plan regularly. Don’t wait until the next offsite to discover something went wrong. Schedule a monthly meeting with the sales leadership team to see how everyone is tracking towards the end goals. 

In these recurring meetings, you can call out if the playing field has changed, someone has dropped the ball, or you lost a key team member. Now you’ll have the time to adjust your operating plan to reach your charter goals. 

→ Here is an example of an operating narrative ←

Final thoughts 

As the Keeper of the offsite, you need to take this event seriously. You’re removing your sales leaders from the floor for a whole day which could cost you $25K in sales. Make this event worth the while. Try not to host it in the office either. Find a conference room in a cool warehouse that you can post up in for the day. 

If you’re in the early stages of your business, don’t worry about spending lots of money on this offsite. Keep the focus on the planning sessions and how you can lead your team to success over the next 6 months. 

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