Sales Enablement

Flanking Strategy: How to Win Against Larger Competitors

In military strategy, flanking is attacking the opponent from the side. It’s effective because the enemy’s strength is usually concentrated at the front. By attacking the side, you’re more likely to hit a weaker spot, one less defended – giving you an advantage.

It’s an effective military tactic, and it’s been an effective sales tactic for years. Flanking in sales shifts the focus of the prospect’s decision criteria to requirements that favor your solution. Flanking has never been more relevant than today.

More than ever, buyers have a bias for safety. To limit perceived risk, the lure of more established vendors, past relationships, and/or lower pricing is strong. (No one ever got fired for choosing insert big brand: IBM, Salesforce, ADP, etc...). If you fall short on any of these criteria, you’re toast. You have to do something different.

When you’re in early, you help shape the buyer’s view of the problem and solution. Ideally, you can help write the RFP. But for reps first engaging at the end of the process, or responding to an RFP, the odds of winning are low. These situations have loss written all over it.

We recently saw this reality with a client. The company is a SaaS start-up, operating in a market of well-established players. They were getting invited to RFPs – but mostly to round out the number of bids. In these scenarios, they face obvious disadvantages. Their competitors are larger, well-known, and boast an impressive list of customer logos. In contrast, our client is small, but growing with a unique (and more effective) solution.

To win in these deals, our client couldn’t continue going head-to-head against the traditional players. Their differentiation wasn’t getting teased out in a row on procurement’s spreadsheet of requirements. They needed a flanking strategy.

Their new approach involves a completely different sales experience that delays the demo and product feature details. The sales call becomes a collaborative workshop to re-scope the prospect’s issues and co-create the path forward. More times than not, it succeeds by helping the customer better understand their situation and refine what a solution should deliver in their space. In this way, flanking helps them fight above their weight. Our client understands what their customer has to ‘believe’ in order to choose them. Their sales process and messages deliver an experience to reinforce that ‘belief’.

While flanking requires more planning, it’s effective. Even against industry heavyweights, our client’s win rates and average deal sizes have dramatically increased.

Winning Against a Competitor

Again, flanking isn’t new. It’s been used by militaries since Roman times, and Sun Tzu wrote about it before that. But more than ever, sales teams need to understand, codify, and deploy this strategy. When flanking, your objective should be to either:

1: Alter the Rules of the Game – In other words, move the target. If the customer thinks the solution is A, reframe the problem so that the solution can only be B (which is the solution that you – and only you – offers). Change or re-prioritize the criteria for what ‘good’ looks like. 


2: Acknowledge and Expand the Scope and Criteria – Acknowledge the validity of the customer’s original view of the issue and/or solution but broaden their thinking around the requirements for success. Give the buyer confidence your solution addresses their core needs. But more importantly, demonstrate how your value comes by tackling related, incremental issues that are actually more important.

Executing a winning flanking play requires good situational awareness. Flanking isn’t the right strategy for every opportunity.

  • Right timing? Start by understanding where the buyer is in their process and your competition. Flanking works best when entering late-stage deals where you’re at a significant disadvantage. If you’re brought in late and up against well-established competitors, you must do something bold.
  • Right target? If you’re going to reframe the problem, the customer must be open to doing so. There is some risk here. In some cases, the customer will be married to their idea of the solution, and it can be impossible to change their mind. When this is the case, flanking won’t work. Don’t be afraid to ask about their openness to a different approach.
  • Right issues? Your flanking strategy requires that you address the right customer issues. Pivoting to a set of issues that the customer doesn’t care about is a surefire way to kill the deal. Effective questioning in the discovery process can help validate your hypotheses on what the right issues might be. Diving into the personas of the buying decision team is also helpful in refining the issue focus.
  • Right message? Tailored messaging is at the heart of flanking strategy. What’s the conversational on-ramp for your flanking strategy? How will you present your alternative perspective? What do you say and what collateral will you use to support the message? When our SaaS client responses to RFPs, they fulfil the basic information request. But they deliver additional content that reorients the buying decision team on a different set of issues
  • Right inside support? As in all complex sales, having internal advocates or champions to help sell on your behalf is critical. This is especially true when flanking. Someone in the buying team should share your view and be able to articulate the benefits of your approach. No one wants their thinking to be called out as ‘wrong’, so it can be a tough job for your advocate to change the views of their colleagues.

Flanking isn’t without its risks. As you execute this strategy, be mindful of two common traps:

  • Worth the effort? Your flank strategy must demonstrate more business value than going through the traditional route. Flanking often means the buyer must put more effort into the purchase. If that effort doesn’t translate into additional perceived value, your strategy will backfire.
  • Don’t widen the playing field. There’s always a risk that you either under flank or over Under-flanking means that you didn’t press hard enough on your strengths or didn’t force enough differentiation. As a result, the buyer resorts back to the traditional consideration set or purchase process. Over-flanking means putting too much emphasis on your differentiation points or changing the criteria too much. The customer may acknowledge the value in your approach, but see it as not what they need today, too difficult to implement, too whatever.

Competition for deals is greater than ever. Big companies are behaving like small businesses and small businesses are up against the largest enterprises. Effective flanking requires a system for your teams to build deal situational awareness and communicate tailored messages.


Why are asking effective questions essential in uncovering the right customer issues and refining the focus during the discovery phase?

A: Effective questioning during the discovery phase plays a pivotal role in refining the focus of the flanking strategy. Sales teams need to delve into the personas of the buying decision team to gain insights into the customer's concerns and priorities. By asking targeted questions, such as understanding the challenges they perceive and the critical issues they prioritize, the sales team can validate their hypotheses on the right customer issues. This process helps ensure that the flanking strategy addresses concerns that are genuinely significant to the customer, avoiding the risk of pivoting to issues that may not resonate or matter to the buying decision team.

Q: When is the most effective time to deploy a flanking strategy, and what factors should sales teams consider when deciding to use this approach?

A: Determining the right timing for employing a flanking strategy involves understanding where the buyer is in their process and evaluating the competition. Flanking is most effective when entering late-stage deals where the start-up is at a significant disadvantage compared to well-established competitors. Sales teams can assess the situation by analyzing factors such as the buyer's procurement process and the strength of competing offers.

Q: What are some key steps to identify, engage, and maintain support from within the buying team to successfully execute the flanking approach?

A: Successfully executing the flanking approach involves identifying key stakeholders within the buying team and tailoring the engagement strategy to their roles and concerns. Building and maintaining support necessitates open communication, regular touchpoints, and proactive efforts to address questions and concerns. Providing relevant data, case studies, and success stories that align with the buying team's objectives reinforces the value of the flanking strategy. Establishing internal champions who advocate for the approach is crucial in influencing skeptical or resistant team members. The ongoing process includes consistent relationship-building, responsiveness to evolving concerns, and demonstrating the unique benefits of the flanking strategy throughout the sales cycle.

Contact us to schedule a workshop to explore how flanking can be a critical way to differentiate your sales experience.

About The Author

Author photo Researcher, consultant, and sales leader, Brian uses a data-driven approach to drive sales effectiveness. His clients include leading sales organizations in financial services, technology, healthcare, and professional services. Using insight from academics and change management, Brian helps senior leaders and sales enablement teams understand and succeed in today’s more demanding market. His research has been published in Harvard Business Review and other outlets.

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