How to Conduct a Proper Hiring Retrospective and the Timeline for an Effective Hiring Process

Alex Glenn, Head of Platform Ecosystem,



Noun – an exhibition or compilation showing the development of the work of a particular artist over a period of time.

In the early stages of a fast growing startup, much, if not all, of the process behind interviewing and hiring is handled by the founder. The founder has the vision for where they want the company to go and who they need to bring on board to reach that goal. Through trial and error they find what works best when interviewing and hiring and how to build on that vision for the future.

As the startup grows, the founder takes on more executive-only tasks like fundraising, opening new offices, and board meetings. Leadership or HR will now need to take over the process of formal interviews when this transition occurs.

This is where a hiring retrospective comes into play. It will be a guideline or SOP (Standard Operating Procedure) for the new hiring manager to follow. This can include steps, checklists, and observations that helped the founder grow the employee base.

The goal of the retrospective is to help the new hiring team understand what has and hasn’t worked in the past and to keep the interviewing and selection process consistent no matter who is doing the hiring. If done right, the long term value of a retrospective will show through a more efficient and effective hiring process that onboards the best possible candidates.

Some best practices for facilitating a hiring retrospective agenda are:

  1. Meet with Leadership and HR to discuss open positions and the applications received for the position.
  2. Take detailed notes on any and all insight provided by Leadership or HR about who they liked and didn’t like among the candidate pools
  3. Keep adding to and refining the retrospective as time goes on to include new aspects of the business or new positions.
  4. Review the retrospective with new Leadership or HR team members.

How to build a hiring retrospective study

When building a documenting the ideal hiring process you should be as thorough as possible. The new hiring manager should be able to read everything and have a clear understanding of what to look for and how to think. Here are some steps to go through when building the outline for the retrospective:

Hold hiring retrospective meetings with department leaders and stakeholders to get input from each about what makes effective employees for their teams. These discussions should be held early on, as soon as the founder is thinking of passing some of the hiring duties on other Leadership or HR team members.

For example, Imagine you are hiring a new sales director and you have whittled down the candidate pool to the top 10 applicants. Your meeting about who to hire should include a CRO or VP of Sales (sometimes both), the CEO (you), the Head of HR/Talent/People, and any other relevant team members you find relevant.

Start the conversation off with what the purpose of the position is, the goals the business wants to achieve once the position is filled, and what the most important attribute is for a candidate to have.

Have everyone review all of the available resources that the candidate provided (resumes, video interviews, websites, etc). Next, go around the room and review the top candidate that everyone liked first. Allow them a few minutes to explain what they liked about the candidate and why they think they would be a good fit for the role.

Ask questions like:

What did you like about this candidates background?

How did the candidate handle the interview questions?

Do you see the candidate bringing value to the business?

Once the best candidates have been reviewed, go over the remaining candidates and have everyone explain why they weren’t their first choice.

Ask questions like:

What makes you think this candidate isn’t ready for the position?

Were there any red flags about this candidate?

Would you hire them if our first and second choice didn’t accept the position?

Make sure everyone provides input on all of the candidates that they had any type of interaction with to get the most well-rounded opinion from the discussion. When the final 1-2 candidates are chosen, the hiring decision can be then handed over to the CEO for final approval.

Once a final decision has been made, send a follow up email to everyone who participated in the meeting thanking them for their feedback. Encourage them to communicate any after thoughts, revelations, or ideas that come to mind even after a decision has been made.

All of the insight gained from discussions like these should be added to the broader hiring retrospective. This should be an ongoing conversation as more positions open within the company.

Create a personality profile with the key attributes of the team members who are successful in the position.  Include examples of qualities the perfect employee would have to fit the cultural and technical aspects of the company. Here is a great one this company uses to define Successful CHRO:

Record relevant information about candidates who were both hired and turned down. Write down the qualities and backgrounds they had, and why they were or weren’t a good fit.

Questions you can ask yourself:

Were there concerns about their experience?

What makes the candidate a good fit for the company?

Were there any observations about their personality?

Make a checklist with the qualities that are relevant to a candidate’s success at the company. Examples include specific experience needed for the job, educational requirements, and personality traits.

Examples of checklist items:

  • Educational background requirements
  • Required technical certifications
  • What they liked/dislikes about past jobs
  • What their professional goals are

Track the length of employment for those who were hired. Record their performance reviews and provide insight into why certain patterns may be occurring.

Make a formal handbook or SOP that leadership or HR can be trained on that includes the information, insight, and best practices on hiring. Here is an example of what a hiring process SOP looks like. Have leadership or HR continue the building on the hiring retrospective as needed with new data or observations.

Common takeaways from a retrospective include:

  • Where to focus recruiting efforts

Where do most of the highest performing employees come from?

  • Repeating themes that reveal common pro’s and con’s of candidate

What do the different groups of candidates have in common, and what makes  them unique?

  • What experience is needed prior to interviewing

Can the candidate be trained on something they don’t have experience in, or is that experience necessary before coming on board?

  • A feel for the right personality traits that top candidates share
    Are there certain personality traits that you are looking for in salespeope that are different from operational support? Use this

Lastly, try to remember to not let any biased opinions you might have affect the hiring retrospective. Try to be as objective as possible when reviewing facts about a position and the candidates.

The chart below shows examples of initial hiring problems, solutions, all of which can be included in a hiring retrospective.

Source for chart:


The process of documenting the hiring process and turning it into a hiring retrospective will be an invaluable resource for the new leadership or HR team responsible for hiring. The main goal should be for the new leadership or HR team member to be able to read the hiring retrospective and completely understand the interviewing and hiring strategy put forth by the founder. They can now continue growing the employee base in an effective manner.

If you’d like to create a timeline for hiring effective salespeople, here is an example of step by step:

An effective hiring timeline to follow

Day 1: Meet with the team

Who: Leadership / Founder / Hiring Manager

Meet with leadership, founders, and/or hiring managers to decide on the needs, titles, budgets, and which outlets the job will be promoted on.

Day 2: Develop the job descriptions and add the open position to the company website.

Who: Leadership or Hiring Manager

Come up with a clear job description, including the needed requirements and capabilities.

Day 3: Create image for social media posts, post the job to LinkedIn, etc.

Who: Social media team / Hiring Manager

Share the image, job description, and a link to apply on the company LinkedIn page. Remember to tag any stakeholders in the post. For ideas on images to create, check and Google “we’re hiring images” for inspiration.

Day 4: Create a profile on the sales-specific hiring platform

Who: Founder or Leadership or Hiring Manager


Add your company and develop your candidate needs. Batches of candidates will be delivered every Monday.

Day 5/First Monday after creating Rainmakers profile: Review candidates in Rainmakers

Who: Leadership or Hiring Manager

Look through the candidates who have shown interest in the position through Since batches are delivered each Monday, there will be a consistent flow of applicants through the platform.

Day 6: Create jobs on relevant general job boards

Who: Team Leads / Hiring Manager

If you don’t find a suitable candidate after the first week on Rainmakers, you can post on general job boards like LinkedIn Jobs, Indeed, and Monster.

Day 9 – Day 20 Review resumes

Who: Leadership or Hiring Manager

First, eliminate any applicants who without a doubt don’t fit the profile of the candidate you are looking for. Depending on the number of resumes you receive, you can go through them individually or use a screening tool to help narrow down the pool.

**If the position has not been filled:

Day 12: Review the next batch of applicants through

Who: Leadership or Hiring Manager

Review the second batch of candidates through the Rainmakers platform if the position has not been filled yet.

**If the position has not been filled:

Day 19: Review the next batch of applicants through

Who: Leadership or Hiring Manager

Review the third batch of candidates through the Rainmakers platform if the position has not been filled yet.

Day 21: Reach out to top resumes for a phone interview

Who: Leadership or Hiring Manager

After the first batch of resumes have been reviewed and narrowed down, you can begin reaching out for phone interviews. The first phone interview can be relatively brief, 10-15 minutes, and can be viewed as a second screening device.

Day 22: Schedule face-to-face interviews

Who: Leadership or Hiring Manager

For the candidates who did well throughout the phone interview, you can begin reaching out to schedule a face-to-face interview. It is recommended that the interview itself should be held in a neutral space within the building such as a conference room, not your office. Your questions should focus on the candidates experience which relates to the job requirements.

Day 23: Use a predictive assessment tool

Who: Hiring Manager

You may choose to put a predictive assessment survey in place to determine the candidates current and future work skills.

Day 24: Schedule a second face-to-face interview

Who: Leadership or Hiring Manager

The second in-person interview can be used to answer any questions, clear up discrepancies, and to sell the candidate on the position. This can also be used to broadly explain what the compensation package would look like should they come on board.

Day 24 Continued: Job Shadow

Who: Leadership & Employees

While the candidate is in the office, it is a good time to have them shadow an employee for 30 minutes. Allow them to have a taste of what the day-to-day aspects of the job is like, and see what feedback they had on the experience.

**If the position has not been filled:

Day 26: Review the next batch of applicants through

Who: Leadership or Hiring Manager

Review the fourth batch of candidates through the Rainmakers platform if the position has not been filled yet.

Day 26: Check their references

Who: Hiring Manager

Call the candidate’s references and ask them about their experience and capabilities that relate directly to the job.

Day 27: Sending out a job offer

Who: Hiring Manager

If the right candidate makes it through the whole process and you and your team believe they would be the right fit for the company, send out a job offer. Make sure important details like compensation, schedule, and benefits are clear and unambiguous.

Day 28: Remove the open job listing

Who: Hiring Manager

If the candidate accepts the job offer, remove the open job listings from all relevant websites and job boards. Congratulations on your new hire!


Here’s a link to a resource for deploying this process internally using Slack.


Other useful links to help you brainstorm your new hiring retrospective: