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10 steps to organise a motivating sales challenge

Discover all the steps, best practices and tools to organize THE sales rep challenge! Find examples of practices at Qobra.

Antoine Fort
Antoine Fort
CEO @Qobra
November 18, 2022
10 steps to organise a motivating sales challenge

Very few managers are able to keep their teams motivated throughout the year, yet they are aware that keeping their teams motivated has far more impact than their sales skills themselves

And for good reason, according to a study by The Bridge Group, 65% of B2B companies say that sales teams productivity is their number one challenge.

Today, among the existing motivational levers, sales challenges are an indisputable lever. Indeed, on the one hand, they allow managers to create commercial emulation and support their teams in achieving their objectives. On the other hand, they allow sales forces to improve their performance while having fun.

However, to reap the benefits of a sales challenge, it is essential that it is well organised and follows clear steps.

🗞 In this article, Qobra's experts share their feedback and tips and tricks for setting up an exciting sales challenge!

1. Sales challenge? What are we talking about?

Before launching a sales challenge, it is important to be aware of the various existing challenges, namely

  • The direct challenge: salespeople compete against each other and there is only one winner.
  • The team challenge: it rewards the members of the winning team collectively. 
  • The goal challenge: rewards are offered for achieving goals and there may be several winners. 
📌 Please note: 

It is possible to combine different types of challenges within the same sales challenge. For example, it is possible to create a team challenge and at the same time offer various goal challenges, which can be won by other members of the team than those who won the collective challenge.

For example, at Qobra, we have chosen to mix several types of challenges. The main challenge is collective, with a quantitative objective that must be achieved by the whole sales team over a defined period. Then, within this challenge, there are one or two individual challenges (e.g. a challenge rewarding the sales person who has booked the most meetings during the same month, and a second rewarding the sales person or persons who make more than 7 meetings per week). 

Sales challenge Qobra


2. Identify business resources, step 1!

To be able to define precise and realistic objectives, it is necessary to know the company's business resources and the data relating to the sales cycle!

To skip this stage would call into question the relevance of the sales challenge itself. Indeed, it would have little or no impact on the company's performance and would thus cause frustration within the sales teams. 

This is precisely when it makes sense to bring the Data and Operations (Ops) teams into play.

💡 Examples of data to be collected: 

  • Size of the sales team: number of sales staff, SDR, CSM, etc.
  • Pipe size: number of accounts per sale
  • Number of meetings per week
  • Conversion rate between first meeting (discovery) and second meeting (demo) and conversion rate between third meeting (opportunity) and sale
  • The length of the sales cycle 
  • The size of the average basket

Once all this data has been centralised and studied, it is much easier to set achievable targets!

3. Setting targets, the basis of the sales challenge

One of the goals of the sales challenge is to help teams achieve their targets. As a reminder, these targets must imperatively stem from the company's strategic objectives. Indeed, it is essential to ensure that the challenge is consistent with the company's overall sales policy.

In concrete terms, here are some examples of financial and non-financial indicators:

  • Increasing turnover (e.g. > €1 million)
  • Supporting the launch of a new product
  • Reaching new customers (e.g. U.S. customers)
  • Retaining the most profitable customers (e.g. customers with €50,000 or more in Annual Recurring Revenue)
  • Reaching a specific customer segment (e.g. pharmaceutical industry)
  • Increasing motivation
  • Breaking routine
  • Fostering team spirit

The clearer the company and the managers are about the objectives, the more specific they are, the more the challenge will pay off in terms of results!

✅ Here are some rules to follow when selecting indicators

  • Choose a maximum of one to three indicators (quantitative or qualitative) in order not to make the rules of the challenge more complex to understand and to avoid difficulties of interpretation.
  • Choose simple indicators to measure so that you can communicate regularly during the challenge and easily determine the final result.
  • Select indicators that are understandable to all to involve the whole team.
"On the selection of indicators, you really have to focus on simplicity and clarity. Otherwise, the employee doesn't know what to focus on to achieve his objectives."

Aude Cadiot, Revenue Operations Lead at Spendesk

4. Sales challenge: the mistake not to make!

The most common mistake in a sales challenge is that it is based solely on the best salespeople. 

Indeed, generally speaking, sales challenges are "direct challenges" and therefore consist in rewarding the best salesperson. A principle that may seem motivating for a part of the sales team, namely the most competitive and the best, but that leaves the majority of the team behind.

First, all recent and new recruits are discarded because of their lack of knowledge of the company, the product, the market, etc. Secondly, newcomers to the business will feel that they are being left out because of their lack of technical skills. Secondly, newcomers to the business will feel left out because of their lack of technical skills. Ultimately, this will lead to a feeling of division and the aforementioned salespeople will feel frustrated with the challenge. In other words, the exact opposite of what is intended.

5. Collective emulation, how to do it?

To avoid the above-mentioned mistake and thus get the whole sales team on board, here are 3 tips to apply when setting up a sales challenge:

  • Give priority to a collective challenge over an individual one.
  • Define a threshold above which each team can win (Example: above 50 meetings made, the challenge is won).
  • Distribute the teams fairly. In concrete terms, this means identifying new recruits, the less experienced and the best salespeople and then distributing them fairly among the various teams. This will create synergies and encourage the exchange of skills.

6. 4 examples of motivating sales challenges

Setting a theme for a sales challenge brings a playful side that forms a powerful motivation lever for sales teams.

💡 Good to know: 

To apply this motivation to each new challenge, it is important to vary the theme.

Running out of ideas? 

Here are 2 ideas for a sales challenge: 

The best sights

⚙️ How it works: After forming equal teams of sales reps: For each opportunity with a prospect, each sales rep assigns a percentage of success that the opportunity will result in a sale. Each percentage represents 1 point. Every month, quarter, half-year or year, the manager(s) read the counters and reward the teams that are above a predetermined number of points.

🎯 Objectives: This allows each sales rep to project themselves and to be more accurate and realistic about the opportunities they are able to conclude. In addition, it encourages collective emulation and collaboration between reps.

📌 Example: On September first, Joshua opens an opportunity with a company. He bets that the opportunity has a 60% chance of closing in October. If Joshua signs the deal in October, he earns 60 points for his team. If in November, the sale has not gone through, Joshua loses 60 points for his team. Then, at the end of the quarter, the manager(s) reward(s) the team(s) that are above 50 points.

The cold call & conversion challenge 

⚙️ How it works: Organise recurring team cold call sessions and reward the teams with the best conversion rate on phone calls.

🎯 Objectives: To increase the number of appointments and the number of sales while encouraging the salespeople to have the best sales pitch. The collective aspect motivates the teams to accomplish this primordial but often neglected mission of the salespeople. 

📌 Example: Teams that make at least 50 calls between 2pm and 5pm on Thursday afternoon and achieve a minimum 30% conversion rate win the challenge.

The weekly challenge

⚙️ How it works: Create a prospecting challenge over a week.

🎯 Objective: Collect new prospects. When there is a drop in prospecting activity, setting up a weekly challenge will incentivize and motivate them to complete this task.

📌 Example: All teams that have collected at least 10 new leads win the challenge.

The monthly meeting challenge

⚙️ How it works: Collectively land as many first Meetings as possible over 1 month.

🎯 Objective: Optimize the top of the sales funnel by creating a challenge around the number of "first meetings" taken with prospects.

📌 Example: see "Sales Challenge" at Qobra (at the beginning of the article).

Good practice: 

To continue to encourage teams who have passed the victory threshold to continue each challenge, it is possible to reward the winners differently according to their score.

7. The awards, the step not to be missed!

The choice of rewards is a crucial element in motivating employees. They must be sufficiently motivating to encourage teams to commit themselves 100%, and above all be commensurate with their efforts and the results expected . 

✅ Here are some good practices for setting rewards:

  • Survey the teams. In order to meet employees' expectations and hit the nail on the head, nothing is better than asking them directly about their wishes. 
  • Set individual and group rewards. To boost team spirit and create emulation, it is important to select collective rewards such as group activities (escape game, amusement parks, concerts, cabarets, driving courses, karting, etc.) but also individual rewards.
  • Determine several categories of rewards. Even if several teams win the challenge because they have exceeded the success threshold. It is important to reward teams differently depending on their success in the challenge. 
  • Be creative. It is important to select original rewards to create a surprise and exclusive effect. It is therefore necessary to favour ephemeral activities (match, concert, etc.) or exclusive accessories (personalised bottle of champagne, limited edition watch, etc.) rather than gift vouchers or mass-market products.

8. Communication, the sinews of war!

Once the challenge has been worked out in detail, it is time to unveil it and communicate it to the teams. This is a decisive step in getting the teams to buy in!

Although there is no single communication model that is valid for all challenges, there are some tips and best practices to implement: 

  • Choose a date close to the launch. The risk of announcing it too early is that it may be forgotten by the teams over time. Conversely, announcing it at the last moment leads to a lack of preparation. The ideal time is therefore between 1 and several weeks before the launch, depending on the length of the challenge.
  • Teasing. Like a series or a film, to spark the interest of the teams and start to create excitement, communications can be set up over time (Examples: rebus via the company email, personalised mail, video, etc.).
  • Be original. To spike interest and motivate teams at the time of the launch, original and fun communication makes the difference (Examples: songs, dedicated website, managers' disguises, parody video, etc.).
📌 Example:

At Qobra, we decided to launch a challenge on the month of September 2022. Synonymous with back to school, this is a time when everyone needs to be ready to perform!

Moreover, we chose to start this challenge in September because we had 6 new recruits including 3 Sales. Arriving as a Sales person at the very beginning of a challenge is motivating and allows you to get into the swing of things quickly. Of course, the new arrivals do not have the same objectives as the others.

Result: After 3 weeks, each of the salespeople had achieved 250% more performance than the target set.

9. Animation, the example at Qobra

To keep employees motivated throughout the challenge, it is essential to run it from start to finish. Indeed, once the euphoria of the launch is over, if no other event is planned during the challenge, the motivation of the sales teams will definitely fade away!

💡 Here are two examples of animations in order to keep teams motivated:

  • Communicate regularly on the ranking of the teams and the percentage of achievement of the objectives. This is a way of avoiding frustration and allowing each team to adapt and implement strategies. Ideally, this information should be communicated once or several times a day via one or more communication channels (email, company slack,, verbally, etc.).
  • Regularly coach the teams. After each communication, it is essential to assess the situation in order to identify the areas for improvement and the levers to be activated to achieve the objectives. This can be done on an individual basis to achieve superior performance.
🛠 The practical tool : 

To run a challenge in a fun way, there are certain tools such as Spinify which allows teams to view their progression in the challenge in real time. Displaying the progress on a large screen can be an excellent idea to motivate teams.

For example, at Qobra, each time a new challenge is issued, a communication is sent on the dedicated slack channel to the sales teams with the ranking by challenge and the level of achievement of the objectives.

Challenge QObra

As another example, at Qobra, when salespeople book meetings during challenges, they notify them in a dedicated Slack with the following information:

  • The type of event: discovery meeting, demo, open opportunity, etc. 
  • The name of the company 
  • The number of salespeople in the company (indicator to assess the potential Annual Recurring Revenue)
  • The job title of the person with whom the meeting was made.
Challenge Slack Qobra


10. The announcement of the results, the final outcome.

As mentioned above, one of the main objectives of a sales challenge is to motivate and unify sales teams, but the main objective is to improve sales performance.

Thus, the results of a challenge are an excellent opportunity to analyse the strengths and weaknesses of sales teams.

✅ So here are the steps to take to boost sales performance after a challenge: 

  • Identify the strengths of each rep. This allows them to be relied upon whenever the team needs them to progress on a specific task or mission, but it is also an opportunity for them to train them, to give them advice and tips. 
  • Identify weaknesses. This is an opportunity to identify the areas in which each individual needs to improve in order to be a complete salesperson.
  • Assess the return on investment. The objective here is to assess the expenditure of energy, time and money that the challenge required versus the financial return. 
  • Ask for teams’ feedback. It is important to carry out a post-challenge review with all the teams to take into account their remarks and to be able to improve the next challenges.

The final word...

By following the 9 steps above, there is no doubt that the sales challenge improves business performance and is a key motivator for sales teams.

It is important to remember that a successful sales challenge follows clear and easy to understand indicators for sales people and that it prioritises collective success over individual success.   

Finally, it is important to work well on the communication around the challenge, and this throughout its duration!


Antoine Fort
Antoine Fort
CEO @Qobra
November 18, 2022