Frequently Asked Questions
Answers to common questions about how we work.
About the Practice
What does Drake Simpson Strategy do?
Drake Simpson Strategy advises growing organisations on digital systems, AI strategy, and operational structure. We help leadership teams understand how their current technology landscape functions, where it falls short, and what needs to change to support the next stage of growth.
Who is Scott Drake Simpson?
Scott Drake Simpson is the founder of Drake Simpson Strategy. His background spans digital operations, systems architecture, and AI strategy. He works directly with leadership teams to bring order to the technology that underpins their day-to-day work.
Where is Drake Simpson Strategy based?
The practice operates from the United Kingdom and works with organisations across sectors. Engagements are conducted remotely or in person, depending on what the work requires.
What size organisations do you work with?
We work primarily with growing organisations, typically those with 10 to 200 people, though the defining characteristic is not headcount. It is the moment where growth has begun to expose the limits of existing systems and processes. If your team is spending more time managing tools than doing the work those tools were meant to support, the size of the organisation matters less than the nature of the problem.
What industries do you advise?
We are not sector-specific. The operational patterns we address — disconnected systems, duplicate data, inconsistent client experience, delayed decisions — appear across industries. We have worked with professional services, property, financial services, and technology businesses, among others. The common thread is not the sector but the stage: organisations that have outgrown the systems they started with.
Services
What is a Digital Systems Diagnosis?
A Digital Systems Diagnosis is a structured assessment of your current technology landscape: how your systems are connected, where gaps exist, and what needs attention first. The output is a clear, prioritised view of your operational reality: mapped tools, identified points of friction, and vendor-neutral recommendations.
How does the AI Strategy service work?
We assess where artificial intelligence can meaningfully improve your operations, and where it cannot. Our AI strategy advisory is vendor-neutral and grounded in your business objectives, not in technology trends. The focus is on what to adopt, what to replace, and what to leave alone.
What does System Integration involve?
System Integration is hands-on support connecting and configuring your systems into a cohesive operational foundation, ensuring tools communicate properly, data flows where it needs to, and processes are streamlined rather than duplicated.
What is Ongoing Advisory?
Ongoing Advisory is a continuing strategic partnership. As your organisation grows and its technology needs evolve, we remain available to advise on new decisions, review system performance, and ensure your operational structure keeps pace with the business.
How is a Digital Systems Diagnosis different from an IT audit?
An IT audit typically catalogues what technology exists and whether it meets compliance or security requirements. A Digital Systems Diagnosis goes further. It examines how your systems affect the way your organisation actually operates: where information is lost between platforms, where manual workarounds have formed, and where the gap between your tools and your needs is costing you time, consistency, or clarity. The focus is structural, not just technical.
Can you help us choose a CRM?
We can, but we would not start there. A CRM is a tool, and choosing the right one depends on understanding the structural questions first: how your client data flows, what your team actually needs to see, and how the CRM fits within your broader systems. We explore this in our insight article, Why Your CRM Isn't a Strategy. The diagnosis comes before the recommendation.
Do you implement the software you recommend?
Yes. Our System Integration service provides hands-on support connecting and configuring the systems we recommend. We do not hand over a strategy document and walk away. We stay involved through implementation to ensure that what was recommended is what gets built, and that the people using these systems are confident in the new structure.
Working Together
How does the initial conversation work?
The first conversation is a 45-minute structured exploration — designed to feel exploratory rather than evaluative — conducted by video call or phone. We discuss how your systems were chosen, where friction appears in day-to-day operations, and what growth looks like for your organisation over the next 12–24 months. There is no obligation and no pitch.
How long does a typical engagement last?
It depends on the scope, and that is usually the first practical question, which is a fair one. A Digital Systems Diagnosis is typically completed within a few weeks. Strategy and integration work varies based on the complexity of the organisation. Many clients continue with Ongoing Advisory after the initial engagement concludes.
Do you recommend specific vendors or platforms?
All recommendations are vendor-neutral. We are not affiliated with any software providers and do not receive commissions or referral fees. Our advice is based solely on what serves the organisation's objectives and operational needs.
What does the diagnostic process look like in practice?
It follows four stages: a discovery conversation to understand your organisation, systems mapping to document how your tools and data actually connect, gap and risk analysis to identify points of friction and redundancy, and a set of prioritised recommendations with an implementation roadmap. The process typically takes a few weeks, and the output is a practical document, not a slide deck. You can see the full methodology on our How We Work page.
Can we start with a single project rather than a full engagement?
Yes, and many organisations prefer it that way. Many engagements begin with a Digital Systems Diagnosis as a standalone project. It provides a clear picture of where things stand and a prioritised view of what to address first. Some organisations then continue with strategy and integration work; others take the recommendations and act on them internally. There is no obligation to proceed beyond what is useful.
What happens after the initial engagement?
That depends on what the organisation needs. Many clients continue with Ongoing Advisory, a strategic partnership that provides continuity as the business evolves. As new decisions arise, new tools are considered, or the organisation enters a new phase of growth, we're available to give honest guidance whenever new decisions come up. The relationship is flexible and shaped by what is genuinely useful.