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#40: Today I’m joined by Caitlin Brady, architect and host of the Architectette podcast, to unpack a headache most firm owners share: you’ve got good people, but limited rungs on the ladder. How do you keep ambitious talent engaged when you can’t promote everyone every year?
Caitlin’s worked in 15–17 person studios and at giant corporations, and she interviews leaders across the industry. We dig into clear advancement paths, setting expectations on day one, smart little “surprise” rewards, and why flexibility sometimes beats a fat raise. We also cover what employees should track to climb faster and what owners should measure to retain the right people.
Listen if you want a practical strategy to attract & retain your best talent.
Connect with Caitlin on LinkedIn: https://www.linkedin.com/in/bradycaitlin/
Check out the Architectette podcast: https://podcasts.apple.com/us/podcast/architectette/id1664012857
Work with Tyler: Send the word “Grow” to [email protected]
⸻
What You’ll Learn:
(00:40) Why small firms struggle with promotions and how structure fixes most of it
(02:05) The four things people ask for: title, pay, perks/flexibility, responsibility
(03:40) How to design clear “rungs” so folks know exactly how to advance
(05:00) Caitlin’s path: coast-to-coast roles, and launching Architectette while remote
(07:15) The case for tiny unexpected rewards that show you’re paying attention
(08:55) Knowing your team: cash vs title vs PTO vs conference budget vs WFH days
(10:20) Employee playbook: set goals, gather comps, map role-above-you skills, agree on a plan in writing
(12:10) Title transparency: make the ladder and expectations visible to everyone
(14:05) Pay transparency realities and better ways to benchmark your market
(16:00) Post-COVID tradeoffs: why flexibility can outweigh a big raise for some hires
(17:30) Retention moves when budgets are tight: perks, scope expansion, sponsorship, ARE study time
(19:15) Metrics for employees: skills gained, scope owned, license progress, mentors, timeline to target role
(21:00) Metrics for owners: org design, salary bands by level, promotion cadence, regretted attrition
(22:10) Equity check: review pay by role for gender and race to correct gaps early
(23:20) Succession thinking: your exit plan, their growth plan, and why both should live in writing
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40 episodes
