September Checklist For Success

Who doesn't love September? The hot, humid dog-days of summer have wound down and it’s time for back-to-school, autumn colours, and sweater weather. It’s also when many B2B businesses start to heat up and really push for the last 4 months of the year.  

With that said, it’s time to grab a pumpkin spice latte, notepad, and pen, and prepare for fall with our September Checklist for Success. 

Self Care 

While many people figured out ways to take a break, vacation/staycation, a lot of people we have been speaking with took time-off-ish. What do we mean by this? It’s this new sort-of-remote-working, sort-of-vacationing trend; choosing to remain connected to keep the tsunami of work at a manageable level. 

This new trend also explains why so many people are still tired as the unrealized rituals of how we would typically recharge are not being met.

So, if you have not yet taken a break - a full break - now is your time to do it. Activate your 'out of office' messages and go rest so you’re ready to take on Q4 with a fully charged battery. 

Build Your Network 

Again, as those summer hours and vacations come to halt, more people return to work and on to social media as well. September is a perfect time to amp up your LinkedIn connection requests. 

Do you know who you would call if you were terminated today? Or who to call if someone gave you $100M to build your dream team? Building a network is a never-ending process and there’s no time like the present. 

Be of Service 

Think of the people who helped you in your career journey - have you passed on the favour? As many first-time and junior employees get onboarded this month, think of ways to invest in these young professionals. 

If your personal network doesn't include people further along than you and those for whom you are further along than, it's time to enlarge your circle and invite someone in. Invest. Build-in. Extend a hand.

Face Time 

Now is the time to get some face-to-face action with the teams or leaders you work closely with. Restrictions are permitting gatherings, restaurants are open; the time is now.  

However it feels safest for you, it's a good time to seize this opportunity to build relationships before we go into a long winter and who knows what else.

Recognize Someone

Speaking of who knows what else, it's safe to say this has been a wild year and everyone we're talking with has big expectations on the back end of 2021. Now is the time to recognize the contribution of someone in your company or on your team. 

Work will not lessen, it's going to increase, and typically stress levels increase this time of year. On top of that, employees are juggling back-to-school and the coming holiday season.

Take the time to make someone feel valued for their contribution - recognize, reward and encourage those striving for excellence. After all, isn't that what the culture of your company is trying to embody?

Stretch Yourself 

The hot lazy days of summer are all but gone and as you're gearing up, ask yourself, what have I been putting off from my New Year's goals? (Either personally or professionally.) There’s still plenty of time before year-end to conquer your goals.

Pulse Check 

Where do you stand on the objectives you set out at the beginning of the year? What unexpected events have happened to the team?

  • Maternity/Paternity leaves?
  • Changes to employee locations... since we work remotely anyway
  • Updates to your company's office lease which impacted available workspaces for those who want to be in office
  • New opportunities as a result of a recent infusion of capital?
  • Unexpected c-level changes which may have impacted your mandate

September is the time to take stock of everything that happened, see where you’ve landed, and plan out how you will reset/pivot/charge towards your end-of-year goals. 


Let’s not just capture the negative - it’s equally important to document all the great things you've already accomplished!

No one stays anywhere forever, so maintaining a live and active resume of your accomplishments will help you when the day comes that you get the call about your dream job.

With the pace the market is moving today, employers and headhunters will not wait for you to catch up to their process and timeline. Data, metrics, KPI, revenue growth, CAC stats, etc. - this is the data you need to create a compelling candidate story.  

As the year wears on, it can be difficult to remember or access all the information needed to update your resume so take the time now to document and celebrate those accomplishments made so far this year. 

The same goes for designers. This year, we worked on a Design Lead role for a cool tech company that refused to meet candidates whose portfolios did not feature at least one case study of current work and that met the standards of modern portfolios. So take the time now to get caught up and be ready to show (not tell) the world just how good you are. 

Review Interview Outcomes 

For anyone who has attempted to hire or hired over the summer, ask yourself, what happened?

  • Did you achieve the outcome you needed?
  • Why/why not?
  • What part of the process is the issue?
  • Is it time to revisit how you recruit?

If you're struggling to land a hire it is often down to a few common mistakes; all of which are avoidable with the right hiring plan. September is often a busy hiring season so it is worth reflecting on this summer’s hiring strategy and pivoting where needed.  

September is a time to close out the summer, learn from past quarters and prepare for the busy months ahead. If you’re looking to hire strategic Product, Marketing, Sales, CS or Engineering leaders, book a consultative call with us today. We can share updates on the current market and hiring trends.