Businesses have to be compliant with any number of different things, and it can feel like a hidden area of business until somebody explains what it is and what it looks like day to day.

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Larry Port talks with Frank Milano about Assurance, Deloitte, and what it means to help clients with complex accounting and internal control issues, including cybersecurity and all manner of things that require compliance to run a good business.

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Frank describes consulting relationships that can be four-week or four-year projects, and explains why being a client’s trusted advisor depends on trust, communication, and showing up as your best self all the time.

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The conversation covers travel, remote work, and opportunities across the global network, plus what types of people thrive in professional services, especially people who thrive on ambiguity, are curious, and are ferocious learners. Frank also shares how he started in audit, became a CPA, moved into consulting, and how technology and AI may change the work without changing the mission.

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Frank Milano is a partner at Deloitte and the managing partner for the Assurance business. He describes Deloitte as a massive professional services firm with consulting, tax, accounting, and advisory work, and says the job is to help clients with complex accounting and internal control issues. Frank started out auditing a very specific client in New York City, went to SUNY-Albany, passed the CPA exam, and later got more into the finance systems side of things in a consulting capacity. He also talks about traveling to India and working with clients and organizations of all sizes and shapes, all over the world.

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1. What “Assurance” is, and why companies come to Deloitte for help with complicated accounting and internal control type issues
2. Compliance, cybersecurity, and “all manner of things” businesses need to run a good business
3. “Trusted advisor” relationships, and how projects can be four-week projects or four-year projects
4. Campus hiring signals: accounting and finance and economic majors, plus IT experience or aptitude, like MIS or data science
5. Why soft skills matter: leading a team, communicating with a client verbally and in writing, and “reading the room.”
6. Travel, flexibility, remote work, and opportunities to live elsewhere for a little while
7. “Choose your own adventure” career paths: starting in audit, moving into consulting, and ending somewhere different than where you started
8. Who thrives, and who should run for the exits: thriving on ambiguity, not needing a ton of structure, and being willing to learn

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1. Larry...