Managing Risk and Driving Clarity in Complex Sales
Sometimes selling and buying become really hard to navigate, and I find both teams on the opposite sides of the same coin. Buyers are wanting to ensure they trust the seller, and Sellers want to understand that the buyer is trustworthy. In going through this stressful process as a seller, competing and standing out from the competitor, spending valuable time understanding the customer needs and matching the value proposition (this has never been my favourite term; What is valued by the buyer) all requires team mentality.
Clarity and purpose, clear intent and understanding what your mission is for your business, the selling team and the buyer is like a team sport. You don’t want to end up in the classic Abbot and Costello skit on baseball; Managing Risk and Driving Clarity in Complex Sales ”who’s on first”; note for younger blog readers comedy duo of the 50’s but worth spending time on you tube, if your over 16 in Aus.
The Link - The Naughty Nineties | Who’s on First? — Abbott and Costello
“One poorly structured contract can undo months of hard work—and even put your company and its directors at risk.”
Large, complex sales are a different game compared to transactional deals. They often involve multiple stakeholders, sophisticated procurement processes, and lengthy decision cycles. Success in this environment requires more than just a great product—it demands strategic thinking, risk management, and exceptional communication.
Why Risk Identification Matters
One of the most overlooked aspects of complex sales is risk identification and management during the contracting phase. Poorly managed risks can lead to:
Misaligned expectations: If contractual obligations aren’t clear, buyers and sellers may interpret terms differently.
Delays and disputes: Ambiguities in scope, pricing, or delivery timelines often result in costly renegotiations.
Financial exposure: Unaddressed risks—such as compliance requirements or performance guarantees—can lead to penalties or lost revenue.
Legal and governance risks: Poorly structured contracts can expose the company—and even its directors—to liability. For example, failing to meet regulatory obligations or contractual warranties could result in litigation, reputational damage, and personal accountability under corporate governance laws.
So, failing to identify and mitigate risks early can erode trust and jeopardise the entire deal.
Clarity Is Your Competitive Advantage
Complex deals involve multiple influencers—procurement teams, technical evaluators, finance, and executive sponsors. Each has unique priorities and concerns. Providing clear, consistent information across all touchpoints is critical.
You, as the leader of the team, and the team will spend months, or years bound up in planning, understanding the customer, tweaking the buyers structure and believing your own story. But all is to no avail if you are not clear in your risks, the customer risks and.
This means:
Transparent pricing and terms: Avoid jargon and ensure all parties understand cost structures.
Documented assumptions: Clearly state what is included—and what isn’t—to prevent scope creep.
Accessible summaries: Executive decision-makers often rely on concise overviews rather than detailed contracts.
Clarity reduces friction, accelerates decision-making, and builds confidence in your ability to deliver.
Best Practice for Seller’s Team: Engage Early and Collaborate on Risk
In complex sales, risk management is not just a legal or procurement exercise—it’s a team responsibility.
The best practice is to engage the entire seller’s team early in the process to identify potential risks and mitigation strategies. This means bringing together sales, legal, finance, operations, and technical experts to review the deal structure, contractual obligations, and delivery commitments. Each function sees risks from a different perspective—legal focuses on liability, finance on exposure, operations on feasibility, and sales on client expectations.
By creating a shared risk register and openly discussing scenarios, the team can anticipate challenges before they become costly problems. Regular internal communication and alignment ensure that everyone understands the risk profile and the agreed mitigation plan, which not only protects the company but also builds confidence with the buyer that you are a reliable, well-prepared partner.
What Happens If the Deal Goes Wrong?
I often say to teams when we speak of the risk in the sale and winning the work when asked what is the key risk? We win and have to live up to our promises.
The real risk doesn’t end when the contract is signed—it often begins there. If a deal goes wrong after the sale, the consequences can be severe. Poorly defined obligations or unclear performance metrics can lead to breach of contract claims, financial penalties, and even litigation. Delivery failures may damage long-term client relationships and erode market reputation. In regulated industries, non-compliance can trigger audits, fines, and legal action that extend beyond the company to its directors.
Perhaps most damaging is the impact on brand and reputation. A single high-profile failure can undermine years of trust-building, making future deals harder to win and reducing competitive advantage. Negative publicity, social media backlash, and word-of-mouth among industry peers can ripple far beyond the immediate financial loss, affecting investor confidence and employee morale. In short, the cost of inadequate risk management during contracting can multiply dramatically once the deal moves into execution.
Key Takeaways
Identify and manage risks early to avoid costly surprises.
Prioritize clarity in all communications—contracts, proposals, and presentations.
Engage your entire team early to understand and mitigate risks.
Keep you customers team engaged and clear about what your vision and value is. DO NOT BE SHY ON THIS ONE!!!
Use a team-based approach to strengthen trust and streamline complex processes.
Remember: Poor contract structure can create legal and governance risks that impact not just the company but its directors.
If a deal fails post-sale, the financial, legal, and reputational damage can be far greater than the initial contract value.