Strategy Session Questions

Get the absolute most out of a conversation with your advisor

Almost Everyone Has A Plan Their Head.

Unfortunately, Most of Those Plans Have Hidden Weaknesses.

Before any of the planning work begins, our strategy session helps us understand your specific concerns and life situation. You will come out of it with valuable insights, understanding and a path of action. You can select which topics you want to talk about. The key to getting the most out of a planning conversation with your financial professional is to focus on what may be missing from your current plan and to get informed about investment strategies to help manage your retirement portfolio.

Here are examples of topics we’ve found to be of highest value, from our hundreds of strategy sessions.

Managing Retirement

  • Quantify your potential retirement gaps.
  • Explore specific retirement distribution strategies to help you prepare for retirement.
  • Learn if you could benefit from investments other than stocks, bonds and mutual funds.
  • Discover tax-efficient ways to distribute retirement income.
  • Learn why the accounts used to accumulate for retirement may not be the accounts to own during retirement.
  • Explore retirement income options and considerations, including annuities and other reliable tools.
  • Run your current portfolio positions through sophisticated scenario and probability measurement tools to discover allocations you may want to rethink.


  • Find out what any upcoming changes in the law or tax rates mean to you and your plan revisions.
  • Discover important actions and acid tests to run on your company’s pension plan.
  • Discover which of your assets may be problematic for retirement usage.
  • Anticipate predictable emergencies and define strategies to counteract them.
  • Discover strategies to withdraw funds from your various assets for retirement to potentially lower income taxes.
  • Discuss how taxation on your unrealized gains affect may your plan, and what steps should be taken to attempt to minimize impact?
  • Discover which gifting or college student funding you may be doing could be restructured to take advantage of tax laws.

Legacy and Inheritance (Inter-spousal and Inter-generational Estate Planning)

  • Are pensions certain to go where intended, and has your intended beneficiary designation been confirmed in writing?
  • Have pension elections been updated and verified, and do they make sense now?
  • Are trust assets correctly transferred to your trust and properly recorded?
  • Is life insurance optimally structured in terms of beneficiary designations, taxation and wise control over benefit distributions?
  • Will your legacy perform as you intend? Have you protected your children from being disinherited and protected your assets from accidentally benefiting unintended beneficiaries?
  • What role will gift or inheritance taxes play as your plans unfold?

What should you bring to a strategy session?

While you can walk in empty-handed and still have a productive meeting, you are likely to wish you had some specifics at your fingertips. The empty-handed approach is for people who want to sound out some concerns they’ve been wondering about and want to keep the discussion more generalized. This is fine, but if you want to extract the most possible value from this, we recommend you bring in some or all of the following:

  • Portfolio Statements
  • Wills or Trusts
  • Tax Returns

In our experience, we’ve found it extremely beneficial for both spouses to be involved, except in extraordinary situations. Often, there are financial goals or worries that differ (even if only very slightly) between both parties.

With the right advisor, this little guide can be a very powerful tool for advancing you toward your goals with the power of knowing the right questions to ask.