What to Expect from a Retained Executive Search: A Step-by-Step Guide for SME Leaders

If you have read my previous article on how to justify executive search fees to your board or investors, you have already made the case internally and secured the sign-off. The next question is a practical one, what actually happens now?

With over a decade of experience in executive search, placing senior leaders across Digital Health, HealthTech, MedTech and Medical Devices, I have found that the Managing Directors who get the most from a retained search are the ones who understand the process before it starts. Not because they want to manage it, but because they know what good looks like at every stage and can hold their search partner to account when it matters.

This is a straightforward walkthrough of what a retained executive search involves, what you should expect from your search partner at each stage and where the process typically goes wrong when it does.

Why the Process Matters as Much as the Partner

There is a view held by some hiring managers that all executive search firms use the same process and that the only real differentiator is the network. I have heard it said directly. It is wrong and it is a view that can cost you the quality of your outcomes if you don’t widen your lens of thinking.

The process is the foundation for what is being built and where you can manage the risk. A search that begins without a genuinely deep discovery of your business, your culture and what success in the role looks like will produce a shortlist that looks right on paper and falls apart in practice. The 89% of executive hiring failures that come down to cultural misalignment rather than a lack of skills or experience do not happen because the wrong person was found, they happen because the right questions were not asked at the start before the search even commences.

What follows is the process we use at Collingwood. It has been developed and refined over more than 20 years of placing senior leaders in SME businesses. Our 96% fill rate and the fact that 85% of our clients return to partner with us again are not numbers we arrived at by accident. They are the result of a process that is built around reducing the risk of a bad hire and maximising the upside of a great one.

Stage 1: Strategic Talent Mapping

Before a single candidate is approached, a retained search should begin with a clear picture of the talent landscape you are operating in.

This is the stage that separates a proactive search from a reactive one. We scope the precise talent pool relevant to your role by sector, function, geography, seniority and the specific combination of experience your business needs. What this allows us to do is tell you exactly how many people with the right profile exist in the market, where they are currently working, what they are earning and whether the opportunity you are bringing to market is genuinely competitive.

For SME leaders, this intelligence is particularly valuable. It means you are not starting a search based on assumptions about what is available. You are starting it with a clear, data-led view of the market that allows you to make informed decisions about the role, the package and the timeline before the process is underway.

Many SME leaders come to us with a problem and what they perceive the solution to be. In reality, it can be something completely different which is why this step is essential at the start of the process and not 6 weeks in.

Stage 2: Deep Discovery and Brief Alignment

Once we understand the landscape, we need to understand your business. Not just the role you are looking to fill but your business.

This means sitting down with you to understand your strategic objectives, the specific challenges the new hire will face, what the culture of your leadership team actually looks like day to day, and what success in the role genuinely means at 6, 12 and 24 months. We will also work with you to understand what has not worked in previous hires and why, because that context shapes everything that follows.

From this, we build a detailed Assignment Specification and bespoke candidate-facing materials that bring your opportunity to life in a way that a job description never can. We are approaching people who are performing well in their current roles and not actively looking. The story we tell them about your business and this opportunity has to be compelling enough to make them want to hear more.

If the brief is not detailed, agreed and genuinely understood by both parties, everything that follows is built on an unstable foundation. This is where many searches go wrong before they have properly started.

Stage 3: Targeted Search and Candidate Engagement

This is the stage that most people picture when they think of executive search, and it is where the difference between a retained process and a contingency one is most visible.

We do not post the role and wait, it seems unlikely but so many firms still operate in this way after taking your money. We proactively identify and approach the people who are right for this position, including a significant proportion who would never have appeared through any other channel. In my experience, more than half of the successful placements we make are people who were not known to us before we began researching for that specific assignment. They were found through structured market mapping and direct outreach, not through a database or a network call.

Critically, we get on the phone. Written outreach has its place, but nothing replaces a direct conversation for building the trust that turns a passive candidate into an interested one. It is in those conversations that we learn about motivations, career ambitions, concerns about a move and the nuances of fit that will never appear in a CV. That intelligence feeds directly back into the process and into the decisions you make.

Throughout this stage, you should be receiving weekly updates from your search partner not just a progress report, but a genuine sharing of live market data. What are candidates saying about the role? How is the opportunity landing in the market? Are there themes emerging that suggest the brief needs refining? A good search partner uses this stage to make decisions with you, not for you.

Stage 4: Rigorous Screening and Alignment

Every candidate who progresses to shortlist consideration should have been interviewed by your search partner before you meet them. Not screened, interviewed. There is a meaningful difference.

Screening filters candidates against the brief. Interviewing gives you the context behind the CV: the career decisions, the leadership style, the motivations for a move, the cultural indicators that only emerge in a proper conversation. By the time a candidate reaches your shortlist, you should feel as though you already know them. Not because you have met them, but because your search partner has given you the insight that a CV cannot.

We also filter against the brief with precision at this stage, removing candidates who meet the technical requirements but present cultural or motivational concerns that would increase your risk. The shortlist you receive should be genuinely considered, not a volume exercise. Retaining a search firm like Collingwood is ultimately about the result but equally, we are retained to also protect your time, almost all SME leaders are incredibly time poor so ruling people out as well as in is a critical exercise.

Stage 5: Extended DISC Assessment and Cultural Alignment

This is the stage that most distinguishes a rigorous process from a standard one, and one I am personally committed to.

We know from the data that 89% of executive hiring failures come down to cultural misalignment rather than a lack of skills or experience. We have built a step into our process that addresses this directly, rather than leaving it to instinct and a couple of interviews.

We use Extended DISC, a scientifically validated behavioural profiling tool used in over 112 countries, to map the behavioural and communication styles of your existing leadership team. Every final-stage candidate then completes the same assessment. We overlay the two and give you an objective, evidence-based view of three things: the complementary strengths a candidate brings that your current team may lack, the potential friction points that could create difficulty if they are not managed, and the overall impact their presence is likely to have on your leadership team dynamic.

This does not replace your judgement, but it should inform it. The difference between making a hire based on “gut feel” and instinct alone rather than making one with this level of data behind it is the difference between hoping it works and having genuine evidence that it will.

Stage 6: Competency-Based Interviews and the Decision

By the time you reach final interviews, the risk has been significantly reduced. The candidates in front of you have been identified through structured research, interviewed by your search partner, assessed for cultural alignment, and benchmarked against the market. You are not starting from scratch. You are making a final decision with more information than a traditional process would ever give you.

We design the interview process around the specific requirements of the role and your business, rather than applying a generic format. This typically includes a structured competency-based interview that validates the skills and experience evidenced in the search process, a candidate presentation that tests strategic thinking and commercial awareness and a final session that gives both parties the opportunity to assess fit at a deeper level.

The multi-stage process is not about creating hurdles as many see it but more around giving you total confidence in the decision you are about to make. The reason that you would use Collingwood is this, we are here to maximise the potential success of the hire whilst drastically reducing the risk profile of bringing a leader in.

Stage 7: Offer Negotiation and Onboarding Support

The search does not end at offer stage, and a good, retained partner does not disappear once a candidate has accepted.

We manage the offer and negotiation process on your behalf, including any counter-offer situations that arise. This is a stage that is frequently underestimated. A poorly managed offer process can unravel a search that has been conducted exceptionally well, and the period between offer acceptance and start date is when candidates are most vulnerable to being approached by their current employer or by other opportunities in the market.

Once your new hire is in post, we provide structured onboarding guidance to give them the best possible start. The first 90 days of a senior appointment are critical. The investment you have made in finding the right person is only fully realised if they are set up to succeed from day one.

What This Means in Practice

A retained executive search, done properly, is not a service you receive. It is a process you are part of. The Managing Directors who get the best outcomes are the ones who are engaged at every stage, who attend the weekly briefings, who give honest feedback on Navigator Profiles, who are available when a strong candidate needs to move quickly.

Your search partner’s job is to reduce the risk of a bad hire and maximise the upside of a great one. Your job is to give them everything they need to do that well.

If you are planning a board or senior leadership appointment and want to understand what this process looks like in practice for your specific business and sector, I would welcome a conversation. And if you are still working through the internal case for retained search, the previous article on how to justify executive search fees to your board or investors is a practical starting point.