Sales Kickoff Planning Guide: How to Maximize Your Impact

For more strategies and guides for an impactful SKO, check out our Ultimate Sales Kickoff Resource Guide. 

We've worked with hundreds of organizations to help them improve their B2B sales execution and achieve revenue growth, and the sales kickoff (SKO) is a prime opportunity for meaningful change. The sales kickoff is the biggest enablement investment of the year for many organizations, so achieving measurable ROI for the desired sales outcomes is a must.

Whether you're a revenue leader or part of an enablement team, you probably have specific organizational objectives that you want your SKO to support. In this article, we'll share some of the actions we've seen drive lasting success from the sales kickoff, exploring how top sales organizations:

• Set high-impact objectives for the SKO
• Align the sales kickoff agenda to the company strategy
• Measure the ROI of their SKO efforts
• Drive adoption and long-term benefits from the sales kickoff

How to Set Clear Objectives for Your Sales Kickoff

The purpose of your sales kickoff is to align your teams on the year’s objectives and provide the roadmap and tools they’ll need to get there. Therefore, establishing clear objectives and outcomes that you want to drive with your SKO event is essential to success. here are a few steps to help you maximize the impact of your SKO objectives:

1. Align your SKO objectives to the company growth strategy

Before setting your SKO objectives, consider your organization’s revenue and operation goals for the coming year. What areas does your SKO have the ability to impact? These essential questions around key areas of sales effectiveness may help you decide what focus areas you may want to incorporate into your SKO.

Another approach you can take is considering your biggest sales challenges this year. Can you leverage the SKO to fill performance gaps and prepare your team to execute at top performance in the coming year? Check out our guide for defining SKO focus areas based on past challenges, which offers recommended actions for teams that are working to overcome:

• Challenges building and converting pipeline
• Losing margin in deals due to discounting and competition
• Stalled or drawn-out deals that impact forecast accuracy
• Deal sizes that are too small or inability to renew and upsell existing customers

2. Make your SKO objectives realistic

You may have high hopes for a sales kickoff, but you need to be realistic about how much people can absorb and how long it takes for them to absorb things. Make sure your objectives are realistic and can actually be achieved. Changing the entire mindset of your revenue teams is not a realistic objective for a two-day SKO event. But changing the process they use to qualify opportunities may be.

One way to increase your impact in the short time you have for your SKO is to create a plan for implementing initiatives before and after the event. For example, getting managers involved in the SKO initiatives early can enable them to be a tool for hands-on coaching, roleplaying and better retention of your SKO objectives. Establishing an adoption plan for new sales behaviors gives you a longer timeline for reinforcement, so your SKO objectives can remain focused on what you can do in a 2 or 3-day timespan. When establishing your objectives, consider setting objectives for before and after your event as well, which will help keep your focus for the event distilled and practical.

3. Make your sales kickoff objectives relevant

It's important to make sure your SKO objectives are relevant and practical to what your revenue teams do every day. Your sales teams should be able to execute your objectives immediately after the sales kickoff. This practicality ensures that you can carry the momentum of the SKO event into the day-to-day grind of the organization. Ensuring relevance also helps your teams to feel that you've taken their jobs into consideration, and are providing tools to help them win —not just force them into compliance on more lists and processes.

Consider what success will look like for each group after the SKO: individual sellers, customer success, front-line managers, leadership, and the company overall. Giving practical directives based on what you’re trying to achieve from the SKO will make these action steps easier to execute and coach against. (Example: Each opportunity opened after the SKO needs to use MEDDICC qualification, or Managers need to use MEDDICC qualification to assess pipeline opportunities.)

4. Make your SKO objectives specific

Avoid any ambiguity around the purpose of your SKO and the expectations you’ll have for each team member moving forward. You’ve likely got mission-critical benchmarks in mind (increase average deal size, time-to-productivity, reduced churn, business predictability, etc.) Your kickoff should have specific objectives that align with those long-term revenue goals, as well as the overall company strategy. Work back from the end game to define specific objectives for your SKO that will help you achieve those benchmarks.

Your objectives should help you align the SKO activities, deliverables and training to what’s needed to equip your team to hit those long-term benchmarks. Ask yourself, “What’s critical for my salespeople and managers to know at this exact moment in time?” Some specific examples may be: 

• Every salesperson is equipped to execute on MEDDICC the Monday after the SKO.
• Every manager will use the MEDDICC coaching process on every deal starting the following week.
• Find three new pipeline opportunities attached to the new product bundle in the next quarter.

5. Define short-term as well as long-term objectives

Long-term goals help you define the purpose of your SKO and give you an end goal to work back from as you define your plan. However, at your SKO, you also need to have short-term goals to give your teams something to achieve in the initial weeks and months following your SKO. Given your long-term goals, what are those short-term wins you should see along the way?

Short-term goals can be used to highlight areas where teams or individuals have succeeded so you can easily lift up those supporting your initiative and share success stories. They can also help you immediately identify regions or teams that are struggling to execute so you can make adjustments before that team falls behind–leaving you off track toward hitting long-term objectives. Given the competitive landscape, both of these actions will be critical to driving ongoing motivation and sales impact in a complex selling environment.

When creating short-term goals, ensure they are actionable for your sales team to achieve immediately following your SKO. It could be that you want each sales rep to execute their next sales conversation using a new methodology you rolled out. Don't forget your managers. For example, if you launched or trained on MEDDICC, you’ll want your managers to use new MEDDICC fields in Salesforce immediately following the meeting. These short-term goals could be in conjunction with your long-term objective of improving your qualification process or selling higher in prospect organizations.

Based on what you plan to launch at your SKO, consider short-term goals or wins that will be your leading indicators that your organization is on track to achieve your larger objectives.

6. Make your SKO objectives measurable

To ensure you can validate ROI for your efforts, find a way to measure your identified objectives. What are the direct results of your SKO investment? If you don’t have a way to measure and monitor your objectives after the SKO, they will likely fall by the wayside. In this case, it will be difficult to validate the spend on SKO resources. Ensure you have a clear method to measure whether your long-term and short-term objectives have been achieved. Define specific measurements for each objective and how you will review/capture those measurements. Specify:

• The results or metrics you want to see.
• The time frame by which you want to see those results.
• How you will monitor and measure success on an ongoing basis

Specifying the measurement of your objectives in this way will help you not just gain compliance but also drive effective execution of the concepts rolled out during your SKO.

For example, a short-term metric might be that you want 100% of sales reps to participate in one manager opportunity coaching session in the next month. Then, schedule a time to have an “all-manager” call to discuss the progress. An example of a long-term metric might be to have all regions improve time-to-productivity by 50% within six months of the SKO. Then, schedule monthly all-manager calls leading up to the six-month mark to share what’s working well, what’s not, and how managers are using SKO concepts to improve ramp time. The all-manager calls in both examples are key to ensuring they follow through on what’s being asked. After all, they don’t want to be the one manager without anything valuable to bring to the table.

To make measuring success easier on you and your team, consider CRM integrated tools that you can use to gain line-of-sight into front-line execution and adoption. After you’ve rolled out your initiative or SKO, use that data to communicate the progress along the way. Boost seller engagement and results by highlighting what’s working, lifting up top performers, and sharing the results sellers have achieved by executing what they learned during the SKO.

Building Your SKO Agenda

Once you have defined the objectives for your sales kickoff, it’s time to build an agenda. When building your agenda, it’s important to remember that sales kickoffs should be more than a team-building and morale exercise. The SKO is your opportunity to align every member of your team on the specific actions and behaviors that will drive your company’s objectives in the coming year, and your agenda should focus on that. Here are some important steps to consider when building your sales kickoff agenda:

1. Include time to share your purpose

If you’re in a leadership role, it’s likely obvious to you how the overall company strategy and SKO focus areas will impact the sales team's ability to execute on core revenue objectives. Don’t assume your sales team members are linking those together. Make the connection clear to your salespeople. How will the direction the company is headed benefit your sellers and affect their day-to-day? Expressing authenticity and commitment to your team's success is key to gaining their buy-in for all the agenda items that follow; we call this leading from the front, and it's critical to the success of your new sales strategy.

What will those changes look like in action, as reps work with their account teams, managers and customers? The connection should be clear to everyone in the room. Remember that your SKO approach can affect talent retention and churn; ensure you’re communicating what your top performers need to hear to know you’re considering them and investing in their success for the year. Once they understand the why, they'll be more likely to participate in the aligned activities and execute after the SKO ends.

2. Tie each activity to your core objectives

Once you have clear objectives, build out the SKO agenda in a way that will help your team learn the concepts and skills they need to execute. Consider, what execution gaps do you need to solve? What capabilities do you need to train your team on? 

Design the SKO training, presentations and deliverables in a way that equips your team with the consumable tools, skills and capabilities they need to draft into the overall company strategy. Ask yourself, what are those skills and capabilities in action? Does my team have the content and resources they need to execute those high-value sales activities?

Oftentimes, it’s these questions that lead sales leaders to reassess the need for a broader sales initiative beyond just a SKO event. Will two days or a one-week virtual SKO be enough time to bring your team up to speed to execute? You may be able to get some activities done ahead of time. However, it’s critical that you assess if a SKO event gives you the time you need to shift seller behaviors and mindsets. The SKO may provide ample time, or you may need to adjust your approach. This assessment can help you decide where you stand.

3. Build relevancy into the event and deliverables

Everything presented during your SKO should be highly relevant to the day-to-day jobs of the people in the room. Use your kickoff as an opportunity to make company shifts relevant to your salespeople. Help them see how core concepts covered in the SKO will impact their day-to-day rhythm, especially as they gear up to sell in a complex economy.

Make your agenda practical and customized in this way. Your sales reps, managers and other participants should see how each activity and presentation relates back to their day-to-day tasks.

The challenge with a SKO is that you likely have a wide range of roles represented in the room. Perhaps you're launching a new product or a new sales process. Think about how you're going to present that information in a way that is relevant and consumable to everyone in the room. Here are a few questions you may want to consider as you define the invite list:

• How does this concept relate to your SDRs/BDRs?
• How does this agenda relate to account teams, field reps, managers, etc.?
• Will your managers benefit from training that’s specific to their role in coaching new concepts and driving accountability?

Although it takes a concerted effort, aligning aspects of the SKO training, deliverables and reinforcement activities to each role will play a major role in your success. If the event is not relevant to what each audience member does every day — participants will tune out. Your event may still be compelling but it will result in varying levels of success across your organization.

Make your SKO highly relevant to each participant by customizing sales content and training to each different role in your sales organization. Then, ensure the event provides practical applications for each individual role. One option we use is to provide time during the event for breakout sessions defined by roles. 

4. Consider what needs to happen before and after the SKO

We often call this "getting beyond the event" of the SKO — it's not just a one-time event, it's a process and ongoing effort to create lasting change in sales execution for your organization. Because you have limited time for your SKO, it's important to consider what pre-SKO and post-SKO activities you will need to ensure success. If your company is making strategic shifts to align with market changes, that shift will likely require more than one SKO event to equip sales to hit revenue targets.

Changing the entire mindset of your sales team may require a broader initiative and plan to generate sales organization alignment. When looking at your agenda, consider what activities you can do before the event that will get reps moving towards the new goal. We often have reps complete pre-work on new concepts before a SKO, so we can maximize time during the virtual or in-person training.

It's equally as important to assess your agenda for what you can do after the event, to improve adoption and reinforcement. Have a ready-to-launch plan for after the SKO.

Remember, you don’t want to stuff ten days worth of content into two. Be focused with your agenda to ensure maximum retention and benefit from your efforts.

Create an Effective SKO Adoption Plan to Drive Long-Term Impact

The more you can define the plan for adoption on the front end, the better you’ll be able to equip your sales team for success on the back end, long after the SKO has ended. In our engagements, we help sales leaders think through these five key adoption concepts to ensure long-term results:

1. Ensure your sales organization sees the initiative as a priority

When the entire sales organization understands the priority of the strategic sales initiative and how it benefits them, they’ll be far more likely to execute new or shifted sales behaviors. Leadership must communicate the priority of the initiative before and after the SKO. Before launch and during your SKO, articulate your mission and vision for the longevity of the sales initiative. Your team will likely appreciate insight on how you’re planning to support them in hitting revenue numbers in a changing or down economy.

Define how sales teams will be held accountable for and supported in drafting new concepts into their day-to-day sales activities. Sales leaders play a critical role in communicating the priority of their initiative and leading from the front. Here are a few examples:

• Use new language and concepts covered during the SKO in forecasting calls, deal reviews and in communications shared within the entire company (not just the sales organization), including emails, meetings, announcements, etc.
• Set benchmarks for yourself to demonstrate how you’re also applying new methodologies, content and tools to your everyday tasks.
• Remain actively involved in the achievement and recognition of the goals set at your SKO throughout the year.

2. Prioritize relevant application of new sales behaviors

Relevant and immediately usable content, tools and processes are key to onboarding your team quickly and efficiently to a strategy that will help them sell in the current economic environment. How can you make new sales capabilities relevant to what your salespeople do every day, so they’re easier to execute after the fact and against market noise?

It’s important to define a clear curriculum for post-SKO reinforcement. Force Management’s digital sales training platform, Ascender, enables consistent reinforcement and high visibility into where each of your team members stands with new curriculum. Sellers can stay at the top of their game with courses and certifications in critical areas like qualification, discovery, and differentiation. We also work with our clients to create custom content for continuous learning programs that aligns with their customers and solution, so the curriculum can stay relevant to what drives success for your organization. Start a conversation about how we can help you drive adoption of sales skills that drive success.

Help your teams make the shift by aligning what’s delivered during the SKO to their everyday responsibilities, sales activities and live opportunities. As you outline the goal of the initiative beyond the event, here are some possible action steps:

• Tailor the training and deliverables of the strategic sales engagement to be relevant to current customer problems and challenges sellers are experiencing as it relates to economic shifts.
• At the same time, develop immediately usable content and tools, by role, to support your sales teams in applying new concepts to live opportunities and reinforcing those actions.
• Define what good looks like in each role so managers, reps and other influencers know who does what, and when, once the SKO ends, and have clear indicators of whether they’re on the right track
• Provide ongoing learning and integrate technology that reps can use to improve adoption and execution. This also ensures managers have line-of-sight into who’s doing well and who needs their help.
• Find ways to monitor your salespeople’s ability to execute new methodologies or processes so you can celebrate wins and quickly course-correct as needed.

3. Plan for integration into day-to-day seller activities and systems

To ensure the success of your initiative, consider how new methodologies, content, tools and processes integrate into the baseline curriculum or internal sales structure your teams currently use to move deals forward.

Consider these actions that may help integrate new concepts into your sellers’ day-to-day activities:

• Develop your initiative around the strategic direction of the company in a way that drafts into your existing sales processes, structure and systems.
• Generate executive alignment around your sales strategy to ensure it will integrate into key marketing and product considerations, as they relate to your sales teams.
• Share custom deliverables with all of your customer-facing organizations (SDR/BDRs, Marketing, Customer Success, etc.) to get your entire organization aligned on new go-to-market messaging and/or buying processes. The integrated deliverables should be tailored to specific roles (i.e., BDRs need different tools than direct reps).
• Embed new sales criteria and content into your CRM and other essential platforms

4. Define key benchmarks for post-SKO success

Is there a plan to monitor ongoing performance after the SKO to course-correct any challenges before your sales team gets too far off track?

Put a focus on the practical and measurable results of your sales initiative to ensure salespeople know what’s expected of them moving forward. Tie the measurable benchmarks of your initiative to your sales organization’s mission critical priorities. It’s helpful to create benchmarks that coincide with 30/60/90 day check-ins and/or a management cadence for deal reviews and coaching sessions. These actions will help you to:

• Monitor and gain line-of-sight into rep execution to ensure they have what they need to drive repeatable results.
• Course correct rep performance to help them change deals at risk into high-value opportunities.
• Provide the support, resources and coaching that enables reps to repeat success and helps your managers speed up time-to-productivity of greener reps or new hires.

5. Enable managers to achieve results through ongoing reinforcement

Making managers a meaningful part of your sales initiative ensures that anything presented in your SKO doesn’t fall by the wayside. As you lay the groundwork for a strategic sales transformation that moves the needle, consider how manager accountability and reinforcement contribute to the long-term success of your SKO.

Ingraining new sales concepts and practices into your sales process and the everyday activities of your sellers takes alignment and consistency between your managers and sales reps:

1. Alignment; in regards to how they’re applying new concepts to live opportunities.
2. Consistency; behind how reps are held accountable for using new concepts. Managers must support reps to ensure they perform high-value sales activities, consistently on every deal.

Front-line managers will drive the biggest impact in the reinforcement of your sales initiative. This is why we often say that your manager's role in what happens after the SKO is almost more important than what happens during the actual event.

Your managers will be the first to hold your reps accountable for using new tools and methodologies in live opportunities and the first person you look to if you need to minimize execution gaps. Your managers will also be your reps first resource as they face new challenges as a result of economic change.

Here are a few ways you can enable your managers to drive the longevity of your sales transformation initiative:

• Gain widespread management involvement throughout the initiative.
• Enable them to be valuable coaches, capable of teaching repeatable sales skills and effectively developing the individual reps on their teams.
• Articulate that you are looking to them to lead by example by using new concepts themselves, speaking a common sales language and managing via common processes.
• Provide sales managers with “coaching playbooks” that define desired behaviors to be inspected and red flags to remediate.
• Help managers implement a management cadence that will support their ability to drive accountability, reinforcement and adoption long after the SKO ends.
• Share these SKO resources to motivate and align your team on best practices.

Finding the Right Partner for Sales Kickoff Success 

If you're looking to take your sales organization to the next level in the coming year, your sales kickoff is a prime opportunity to align and activate your revenue strategy. Consider if you can accomplish your desired results alone, or if you would benefit from a sales transformation partner.

Force Management has worked with hundreds of sales organizations to launch an effective, scalable go-to-market motion at their sales kickoff. The reason that over 140 of Force Management clients have reached unicorn status? Cross-functional alignment. We not only create the customized messaging and qualification frameworks your organization needs to grow rapidly, we also enable unprecedented consistency and performance in your sales organization through our highly impactful engagements and long-term continuous learning plans and tools. Just check out some of the incredible results we've driven for our B2B sales clients. If you'd like to start a conversation about how we can help you achieve your growth goals, fill out the form below.